4-Chloroaniline

H301: Toxic if swallowed [Danger Acute toxicity, oral]

H311: Toxic in contact with skin [Danger Acute toxicity, dermal]

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

H331: Toxic if inhaled [Danger Acute toxicity, inhalation]

H350: May cause cancer [Danger Carcinogenicity]

H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P203, P261, P262, P264, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P316, P318, P321, P330, P333+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

H301+H311+H331 (18.2%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

H311 (99.5%): Toxic in contact with skin [Danger Acute toxicity, dermal]

H317 (99.5%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H319 (17.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H331 (99.5%): Toxic if inhaled [Danger Acute toxicity, inhalation]

H350 (99.5%): May cause cancer [Danger Carcinogenicity]

H373 (17.3%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

H400 (99.1%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (99.5%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P203, P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P321, P330, P333+P317, P337+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 214 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

P273, P391, and P501 (click each P-code to see the statement)

H320: Causes eye irritation [Warning Serious eye damage/eye irritation]

H332: Harmful if inhaled [Warning Acute toxicity, inhalation]

H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]

H351: Suspected of causing cancer [Warning Carcinogenicity]

H370: Causes damage to organs [Danger Specific target organ toxicity, single exposure]

H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]

P203, P260, P261, P262, P264, P264+P265, P270, P271, P272, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P308+P316, P316, P317, P318, P319, P321, P330, P333+P317, P337+P317, P361+P364, P362+P364, P405, and P501 (click each P-code to see the statement)

P203, P260, P261, P262, P264, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P316, P318, P319, P321, P330, P333+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Refer for medical attention .

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.

INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:

SMALL FIRE: Dry chemical, CO2 or water spray.

LARGE FIRE: Water spray, fog or regular foam. If it can be done safely, move undamaged containers away from the area around the fire. Dike runoff from fire control for later disposal. Avoid aiming straight or solid streams directly onto the product.

FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2024)

Use water spray, powder, foam, carbon dioxide.

Water, dry chemical, foam or carbon dioxide

Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:

IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.

SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.

FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

Personal protection: P3 filter respirator for toxic particles and chemical protection suit. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Removal of chloroaniline from wastewater by electrochemical treatment is discussed.

Cover with the 9:1 mixture of sand and soda ash. After mixing, transfer into a paper carton, stuffed with ruffled paper. Burn in an open furnace with the utmost care or in the furnace with afterburner and scrubber.

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P024, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids.

PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/

For more Disposal Methods (Complete) data for 4-CHLOROANILINE (7 total), please visit the HSDB record page.

Immediately wash contaminated areas of body with concentrated soap solution. Remove contaminated clothing, dry, then wash with concentrated soap solution or dispose as waste. Contaminated shoes may be disposed of in an incinerator.

It is less hazardous than aniline or mononitrobenzene in industrial exposures. Relatively low vapor pressure, but precaution should be taken to avoid inhalation of vapors.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

For more Preventive Measures (Complete) data for 4-CHLOROANILINE (14 total), please visit the HSDB record page.

Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:

ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Cover with plastic sheet to prevent spreading. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2024)

Separated from strong oxidants and food and feedstuffs.

Storage temperature: ambient.

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

Biological Exposure Indices (BEI) [ACGIH] - Methemoglobin in blood = 1.5% of hemoglobin during or at end of shift. [ACGIH]

1.6 [mg/m3]

17 [mg/m3]

100 [mg/m3]

skin absorption (H); sensitization of skin (SH); carcinogen category: 2

A harmful concentration of airborne particles can be reached quickly when dispersed.

The substance is irritating to the eyes. The substance may cause effects on the red blood cells. This may result in lesions of blood cells and the formation of methaemoglobin. Medical observation is indicated. The effects may be delayed.

Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the spleen. Tumours have been detected in experimental animals but may not be relevant to humans.

Rubber gloves; chemical goggles; protective clothing; dust respirator. (USCG, 1999)

Rubber gloves; chemical goggles; protective clothing; dust respirator.

PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/

NO open flames.

PREVENT DISPERSION OF DUST! STRICT HYGIENE! IN ALL CASES CONSULT A DOCTOR!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles or eye protection in combination with breathing protection.

Do not eat, drink, or smoke during work.

P-chloroaniline appears as a white or pale yellow solid. Melting point 69.5 °C.

Colorless, white, or pale-yellow solid with a characteristic sweet odor; [HSDB] Light tan chips or crystalline solid; [MSDSonline]

COLOURLESS-TO-YELLOW CRYSTALS WITH CHARACTERISTIC ODOUR.

A white or pale yellow solid.

Orthorhombic crystals from alcohol or petroleum ether

Colorless crystals

White or pale yellow solid

SLIGHTLY SWEETISH; CHARACTERISTIC AMINE ODOR

Characteristic sweet odor

450 °F at 760 mmHg (NTP, 1992)

232 °C @760 [mm Hg]

162.5 °F (NTP, 1992)

69-72.5 °C

162.5 °F

235 °F (NTP, 1992)

120-123 °C

>220 °F (open cup)

120-123 °C o.c.

less than 1 mg/mL at 74.3 °F (NTP, 1992)

Freely soluble in alcohol, ether, acetone, carbon disulfide

In water, 3,900 mg/L at 25 °C

Solubility in water, g/100ml at 20 °C: 0.39

1.43 at 66.2 °F (USCG, 1999) - Denser than water; will sink

1.169 at 77 °C/4 °C

Relative density (water = 1): 1.4

1.43 at 66.2 °F

1.429 @ 19°C

4.41 (NTP, 1992) - Heavier than air; will sink (Relative to Air)

Relative vapor density (air = 1): 4.4

0.015 mmHg at 68 °F ; 0.05 mmHg at 86 °F (NTP, 1992)

0.02 [mmHg]

Vapor pressure = 10 MM HG @ 102.1 °C; 40 MM HG @ 135 °C; 100 MM HG @ 159.9 °C

0.071 mm Hg at 25 °C

Vapor pressure, Pa at 20 °C: 2

0.015 mmHg

0.071 [mm Hg] @25 °C

log Kow = 1.83 at pH 7.4

Henry's Law constant = 3.1X10-6 atm-cu m/mol at 25 °C /Estimated/

Stability during transport: stable.

When heated to decomposition it emit toxic fumes of /hydrogen chloride and nitrogen oxides/.

Insoluble in cold water. Soluble in hot water [Hawley].

Aryl Halides

Amines, Aromatic

P-CHLOROANILINE is incompatible with oxidizing agents. Also incompatible with acids, acid chlorides, acid anhydrides and chloroformates. Subject to exothermic decomposition during high-temperature distillation. Incompatible with nitrous acid. (NTP, 1992)

Very vigorous reactions may occur with strong oxidants.

IDENTIFICATION: 4-Chloroaniline (PCA) is a colorless to slightly amber-colored crystalline solid with a mild aromatic odor. The chemical is soluble in water and in common organic solvents. PCA is used as an intermediate in the production of a number of products, including agricultural chemicals, azo dyes and pigments, cosmetics, and pharmaceutical products. HUMAN EXPOSURE: In humans, hemoglobin adducts are detectable as early as 30 min after accidental exposure, with a maximum level at 3 hr. Slow acetylating individuals have a higher potency to form hemoglobin adducts compared with fast acetylators. Excretion in humans occurs primarily via the urine, with PCA and its conjugates appearing as early as 30 min after exposure. Excretion takes place mainly during the first 24 h and is almost complete within 72 h. Data on occupational exposure of humans to PCA are mostly from a few older reports of severe intoxications after accidental exposure to PCA during production. Symptoms include increased methemoglobin and sulfhemoglobin levels, cyanosis, the development of anemia, and changes due to anoxia. PCA has a strong tendency to form hemoglobin adducts, and their determination can be used in biomonitoring of employees exposed to 4-chloroaniline in the workplace. There are reports of severe methemoglobinemia in neonates from neonatal intensive care units in two countries where premature babies were exposed to PCA as a breakdown product of chlorohexidine; the chlorohexidine, which had been inadvertently used in the humidifying fluid, broke down to PCA upon heating in a new type of incubator. Three neonates in one report (14.5-43.5% methemoglobin) and 33 of 415 neonates in another report (6.5-45.5% methemoglobin during the 8-month screening period) were found to be methemoglobin positive. A prospective clinical study showed that immaturity, severe illness, time exposed to PCA, and low concentrations of NADH reductase probably contributed to the condition. ANIMAL STUDIES: PCA is rapidly absorbed and metabolized. The main metabolic pathways of PCA are as follows: a) C-hydroxylation in the ortho position to yield 2-amino-5-chlorophenol followed by sulfate conjugation to 2-amino-5-chlorophenyl sulfate, which is excreted as is or after N-acetylation to N-acetyl-2-amino-5-chlorophenyl sulfate; b) N-acetylation to 4-chloroacetanilide (found mainly in blood), which is further transformed to 4-chloroglycolanilide and then to 4-chlorooxanilic acid (found in the urine); or c) N-oxidation to 4-chlorophenylhydroxylamine and further to 4-chloronitrosobenzene (in erythrocytes). Reactive metabolites of PCA bind covalently to hemoglobin and to proteins of liver and kidney. Excretion in animals occurs primarily via the urine, with PCA and its conjugates appearing as early as 30 min after exposure. Excretion takes place mainly during the first 24 hr and is almost complete within 72 hr. The prominent toxic effect is methemoglobin formation. PCA is a more potent and faster methemoglobin inducer than aniline. PCA also exhibits a nephrotoxic and hepatotoxic potential. PCA was found to be non-irritating to rabbit skin and slightly irritating to rabbit eyes. A weak sensitizing potential was demonstrated with several test systems. Repeated exposure to PCA leads to cyanosis and methemoglobinemia, followed by effects in blood, liver, spleen, and kidneys, manifested as changes in hematological parameters, splenomegaly, and moderate to heavy hemosiderosis in spleen, liver, and kidney, partially accompanied by extramedullary hematopoiesis. These effects occur secondary to excessive compound-induced hemolysis and are consistent with a regenerative anemia. PCA is carcinogenic in male rats, with the induction of unusual and rare tumors of the spleen (fibrosarcomas and osteosarcomas), which is typical for aniline and related substances. In female rats, the precancerous stages of the spleen tumors are increased in frequency. Increased incidences of pheochromocytoma of the adrenal gland in male and female rats may have been related to PCA administration. There was some evidence of carcinogenicity in male mice, indicated by hepatocellular tumors and hemangiosarcoma. PCA shows transforming activity in cell transformation assays. A variety of in vitro genotoxicity tests Salmonella mutagenicity test, mouse lymphoma assay, chromosomal aberration test, induction of sister chromatid exchange indicate that PCA is possibly genotoxic, although results are sometimes conflicting. Due to lack of data, it is impossible to make any conclusion about PCA's in vivo genotoxicity. No studies are available on reproductive toxicity. From valid test results available on the toxicity of PCA to various aquatic organisms, PCA can be classified as moderately to highly toxic in the aquatic compartment. Therefore, a possible risk to aquatic organisms, particularly benthic species, cannot be completely ruled out, particularly in waters where significant amounts of particulate matter inhibit rapid photomineralization. Experiments with Daphnia magna revealed significantly reduced toxicity with increasing concentrations of dissolved humic materials in the medium, possibly caused by reduced bioavailability of PCA from adsorption to dissolved humic materials.

p-Chloroaniline

4 x 10 ^-3 mg/kg-day

Cancer Classification: Group B2 Probable Human Carcinogen

Evaluation: There is inadequate evidence in humans for the carcinogenicty of para-chloroaniline. There is sufficient evidence in experimental animals for the carcinogenicity of para-chloroaniline. OVERALL EVALUATION: Group 2B: para-Chloroaniline is possibly carcinogenic to humans.

para-Chloroaniline

Group 2B: Possibly carcinogenic to humans

Volume 57: (1993) Occupational Exposures of Hairdressers and Barbers and Personal Use of Hair Colourants; Some Hair Dyes, Cosmetic Colourants, Industrial Dyestuffs and Aromatic Amines

TR-189: Bioassay of p-Chloroaniline for Possible Carcinogenicity (CASRN 106-47-8) (1979 )

10/25/78

Equivocal Evidence

No Evidence

The findings of small numbers of fibromas and sarcomas in the spleens of male rats was considered strongly suggestive of carcinogenicity because of the rarity of these tumors in the spleens of control rats. Hemangiomatous tumors in dosed mice may also have been associated with administration of p-chloroaniline. However, it is concluded that, under the conditions of this bioassay, sufficient evidence was not found to establish the carcinogenicity of p-chloroaniline for Fisher 344 rats or B6C3F1 mice.

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

Blue lips, fingernails and skin. Confusion. Convulsions. Dizziness. Headache. Nausea. Unconsciousness.

MAY BE ABSORBED! Further see Inhalation.

Redness. Pain.

See Inhalation.

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as primary toxic effect.

Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

IARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.

5 x 10^-4 mg/kg-day

PDF Document

Likely to be carcinogenic to humans

PPRTV Memo

PPRTV Current

LC50 (rat) = 2,340 mg/m3/4h

LD50 Rat male oral 200-480 mg/kg bw /Purity and vehicle unspecified/

LD50 New Zealand Rabbit male dermal 360 mg/kg bw /Purity and vehicle unspecified/

LD50 Rat oral 0.31 g/kg

LD50 Rat dermal 3200 mg/kg

For more Non-Human Toxicity Values (Complete) data for 4-CHLOROANILINE (10 total), please visit the HSDB record page.

Methylene blue, alone or in combination with oxygen, is indicated as treatment in nitrite-induced methemoglobinemia.

/HUMAN EXPOSURE STUDIES/ In the United Kingdom between 1961 and 1980, chloroaniline, p-toluidine, nitrobenzene, and nitrochlorobenzene were the most common industrial causes of methemoglobinemia. Dermal exposure was a more frequent route of toxicity than inhalation with these compounds. /Chloroaniline/

/HUMAN EXPOSURE STUDIES/ Methemoglobinemia, which is also consistent with the presence of a circulating N-hydroxy-para-chloroaniline metabolite, has been reported in workers exposed to para-chloroaniline and in neonates inadvertently exposed in incubators to chlorhexidine gluconate, which is known to decompose spontaneously to para-chloroaniline ... .

/SIGNS AND SYMPTOMS/ In one plant, average workplace air concentrations at two sites in PCA production were 58 mg PCA/cu m (range 37-89 mg/cu m) and 63 mg PCA/cu m (range 46-70 mg/cu m), respectively. Inhalation and simultaneous dermal absorption resulted in cyanosis, increased methemoglobin and sulfhemoglobin levels, the development of anemia (2 of 6 workers within 4 weeks), and acute intoxication (1/6, who had to discontinue working). In another plant producing PCA from 4-chloronitrobenzene, 14 workers showed a significant fall in hemoglobin and significant increases in methemoglobin, which did not correlate with the air concentrations of PCA (values not given in study report). For comparison, in otherwise healthy patients, levels of methemoglobin in excess of 30% may cause fatigue, headache, dyspnea, nausea, and tachycardia. Lethargy and stupor, as well as deteriorating consciousness, occur as levels approach 55%. Higher levels may cause cardiac arrhythmias, circulatory failure, and neurological depression. Methemoglobin levels higher than 70% are usually fatal.

/CASE REPORTS/ Cyanosis and methemoglobinemia (14.5-43.5% methemoglobin; normal range <2.3%) in three premature neonates (gestational age 25-27 weeks) were reported to be associated with PCA contamination of the incubators (no information on PCA concentration) in Amsterdam. Exposure was by percutaneous absorption or by inhalation of PCA-containing vapor produced by the inadvertent use of chlorohexidine gluconate (0.25 g/liter) as a humidifying agent, which decomposed on heating to produce PCA. A further report describes the same scenario in a neonatal intensive care unit in Copenhagen, showing that premature neonates developed severe methemoglobinemia when exposed to even small amounts of PCA formed from the inadvertent use of a 0.02% chlorohexidine solution as a humidifier in new incubators. The authors estimated that the maximum amount of PCA that the neonate could be exposed to was 0.3 mg/day, provided that all PCA produced was absorbed by the neonate. Thirty-three of 415 neonates (8%) were found to be methemoglobin positive (mean methemoglobin concentration 19%; range 6.5-45.5%) during the 8-month screening period. Of those patients with a gestational age of <31 weeks, 40% were positive; 15 out of 25 neonates (60%) with a birth weight </=1000 g proved to be positive. All the methemoglobin-positive cases started when the neonate was in the new incubator. A prospective clinical study showed that immaturity, severe illness, the time exposed to PCA, and low concentrations of NADH reductase probably contributed to the condition. Fetal hemoglobin is more easily oxidized than adult hemoglobin; further, the delicate skin of the premature neonate is more permeable.

For more Human Toxicity Excerpts (Complete) data for 4-CHLOROANILINE (7 total), please visit the HSDB record page.

/LABORATORY ANIMALS: Acute Exposure/ Nephrotoxicity was also reported in male Fischer 344 rats given a single ip dose of para-chloroaniline (purity unspecified) at 1.5 mmol (191 mg)/kg bw in saline, which induced decreased urine volume, hematuria, elevated blood urea nitrogen and decreased renal cortical uptake of para-aminohippurate... .

LC50 Lepomis macrochirus (Bluegil)l 2.4 mg/L/96 hr /Conditions of bioassay not specified in source examined/

EC50 Chironomus plumosus (Midge, 4th instar larvae; immobilization) 43 mg/L/48 hr /Conditions of bioassay not specified in source examined/

LC50 Brachionus rubens (Rotifer) 100 mg/L/24 hr; static /formulated product/

EC50 Chlorella zofingiensis (Green algae; inhibition of chlorophyll biosynthesis) >200 uM/48 hr; static

For more Ecotoxicity Values (Complete) data for 4-CHLOROANILINE (14 total), please visit the HSDB record page.

/AQUATIC SPECIES/ Toxicity of p-chloroaniline was determined by the 14 day Daphnia reproduction test and the 24 hr median effective concentration (EC50). EC50 values ranged from 0.008-38 ppm. p-Chloroaniline at concentrations (0.0427-1.35 ppm) which were less than the EC50 showed marked effects on the reproduction rate.

/AQUATIC SPECIES/ The influence of enzyme induction on the acute toxicity of aniline and 4-chloroaniline to rainbow trout (Salmo gairdneri) was investigated. For these two xenobiotics, bioactivation reactions are known to occur in mammals. Induction of cytochrome P450 mixed-function oxidase was obtained by ip injection of trout with a mixture of polychlorinated biphenyls (Aroclor 1254). Five days after ip injection with three different doses of Aroclor 1254 (50, 100, and 200 mg/kg), benzo[a]pyrene hydroxylase activity in trout liver microsomes increased five- to six-fold. Cytochrome P450 concentrations in the microsomes were slightly, but significantly, enhanced in two of the three dose levels. The 96-hr LC50's of aniline and 4-chloroaniline were not affected by pretreatment with Aroclor 1254, suggesting that metabolic activation does not necessarily play a role in the acute toxicity of aromatic amines to fish.

/AQUATIC SPECIES/ ...The effect of the applied p-chloroaniline on hepatic cells of zebra fish and additionally exposed rainbow trout (Oncorhynchus mykiss) /was studied/. For both species, exposure to p-chloroaniline concentrations of 0.2 and 1 mg/liter resulted in significant ultrastructural changes of hepatic cells. In later studies on zebra fish with prolonged exposure (31 days), hepatocytes and gills of exposed fish exhibited dose-dependent alterations at p-chloroaniline concentrations of > or =0.05 and > or =0.5 mg/liter, respectively. Pathological symptoms in both liver and gills disappeared almost completely within a regeneration period of 14 days.

/AQUATIC SPECIES/ Dissolved humic materials in the exposure media may have a marked influence on the toxicity of PCA to aquatic species. ...Significantly reduced toxicity for cell multiplication inhibition of Daphnia magna (48-hr EC50) /was found/ with increasing dissolved humic material concentrations, whereas the LC50 for zebra fish remained unaffected in the presence of dissolved humic materials. Among several explanations, the authors discussed reduced bioavailability by sorption of PCA to dissolved humic materials as a possible cause of this effect.

/AQUATIC SPECIES/ In addition to survival and hatching parameters, cytological alterations in liver and kidney of 4- and 6-d old zebrafish larvae (Brachydanio rerio) following single microinjection of fertilized eggs at the germ-ring stage with 5, 12.5, and 25 ng 4-chloroaniline/egg were investigated by means of electron microscopy. Whereas survival remained unaffected, microinjection with 4-chloroaniline disturbed hatching of larvae. Hatching was delayed by microinjection of 12.5 ng 4-chloroaniline/egg and above when compared to controls. Cytological investigations revealed ultrastructural changes in both liver and kidney in a dose- and time-dependent fashion. In the liver, major cytopathological changes included fenestration, fragmentation, and vesiculation of the rough endoplasmic reticulum, proliferation of atypical mitochondria, and atypical lysosomes. Furthermore, myelin whorls, lipid inclusions, and cholesterol crystals were increased, whereas glycogen stores were reduced. Renal tubular cells displayed altered brush borders, proliferation of nucleoli, atypical mitochondria, fenestrated, fragmented, and vesiculated RER cisternae, as well as giant lysosomes. Most of these effects indicate cellular dysfunction (e.g., disturbance of lipid metabolism in the liver), whereas others illustrate general cellular stress-responses to chemical aggression.

2.70e+00

1.10e+01

3.70e-01

6.0E+01(G)

1.60e-04

2.00e-01

5.00e-04

Volatile

9.50e+01

1.10e+03

2.80e+01

6.0E+01 (G)

The substance is toxic to aquatic organisms. It is strongly advised not to let the chemical enter into the environment.

4-Chloroaniline's production and use as an intermediate for the synthesis of dyes, pharmaceuticals, and agricultural chemicals may result in its release to the environment through various waste streams. It is also a widespread soil contaminant resulting from the use of phenylurea herbicide of which it is a degradation product. If released to air, a vapor pressure of 0.071 mm Hg at 25 °C indicates 4-chloroaniline will exist solely as a vapor in the ambient atmosphere. Vapor-phase 4-chloroaniline will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 9 hours. 4-Chloroaniline absorbs light with wavelengths >290 nm and may be susceptible to direct photolysis by sunlight. If released to soil, 4-chloroaniline is expected to have high to low mobility based upon Koc values ranging from 96-1,530. However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group, suggesting that mobility may be much lower in some soils. Volatilization from moist soil surfaces is expected based upon an estimated Henry's Law constant of 3.1X10-6 atm-cu m/mole. However, adsorption to soil may attenuate volatilization. The pKa of 4-chloroaniline is 3.98, indicating that this compound will primarily exist in its nonionic form in the environment. 4-Chloroaniline is not expected to volatilize from dry soil surfaces based upon its vapor pressure. The results of biodegradability screening studies for 4-chloroaniline are conflicting with results ranging from no degradation to rapid degradation using soil, sewage, activated sludge and fresh water inocula. However, the most frequently reported results are that 4-chloroaniline biodegrades rather slowly with acclimation. The reason for the conflicting results may be due to toxicity of metabolic intermediates, differences in concentrations and inocula used, sensitivity of 4-chloroaniline to chemical oxidation, and lack of sufficient acclimation. If released into water, 4-chloroaniline is expected to adsorb to suspended solids and sediment based upon its Koc values. Volatilization from water surfaces is expected based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 36 and 260 days, respectively. However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. BCF values ranging from 0.8 to <20 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. The half-life of 4-chloroaniline under illumination conditions typifying those for US surface waters in summer is 0.4 hour. Occupational exposure to 4-chloroaniline may occur through inhalation and dermal contact with this compound at workplaces where 4-chloroaniline is produced or used. Monitoring data indicate that the general population may be exposed to 4-chloroaniline via ingestion of food and drinking water. (SRC)

4-Chloroaniline's production and use as an intermediate for the synthesis of dyes, pharmaceuticals, and agricultural chemicals(1) may result in its release to the environment through various waste streams. As 4-chloroaniline is a photooxidation product of monuron(6) and a degradation product of 4-chlorophenylurea(2) and diflubenzuron(7), release to the environment is possible as a result of the use of these pesticides(SRC). It is also a degradation product of chlorhexidine digluconate (a hospital disinfectant) exposed to acclimated activated sludge(3). Eleven years after a 2-year application of (14-C)buturon, 4-chloroaniline accounted for 15% of the label(4). 4-Chloroaniline is a contaminant of chlorhexide, which is used in the disinfection of soft contact lenses(5) and therefore 4-chloroaniline may be disposed of by soft contact lens wearers(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 96-1,530(2,3), indicate that 4-chloroaniline is expected to have high to low mobility in soil(SRC). The pKa of 4-chloroaniline is 3.98(6), indicating that this compound will primarily exist in its nonionic form in the environment. However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(4,5), suggesting that mobility may be very low in some soils(SRC). 4-Chloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.071 mm Hg(7). Volatilization of 4-chloroaniline from moist soil surfaces is expected(SRC) given an estimated Henry's Law constant of 3.1X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.071 mm Hg(7), and water solubility, 3.9 g/L(8). However, adsorption to soil is expected to attenuate volatilization(SRC). (14)C labeled 4-chloroaniline was applied to soil in lysimeter, corresponding to 1.25 ppm to a depth of 10 cm, and barley was sown(9). After 20 weeks, a total of 32.8% of the radiocarbon applied was recovered, corresponding to 32.4% in soil, 0.3% in plants, and 0.1% in leaching water (9). Radioactivity in soil consisted of 30.8% unextractable residues(9). When 4-chloroaniline (30 ppm) was incubated in Guelph loam with water added to 60% water-holding capacity, levels declined rapidly for two weeks after which time the rate of loss decreased(10). The percent of 4-chloroaniline remaining after 2 and 8 weeks were 45 and 25%, respectively(10). Mineralization occurs most rapidly in the early weeks of incubation with as much as 7.5% degradation to CO2 occurring in 6 weeks and 17% occuring in 16 weeks(10). Most (70-90%) of the 4-chloroaniline is transformed into unextractable residues and there is no significant leaching out either vertically or horizontally into surrounding layers of soil(10). Experiments were conducted in which (14C)4-chloroaniline was incubated under outdoor conditions for 20-25 wk and stepwise extractions conducted in order to establish the binding sites and degradability of the chemical in the different soil fractions(11). The total recovery of 14C was 32.4% of which 95.1% was as bound residues(11). The concns (ug equivalents to parent compound per g dry soil fraction) of bound 14C in the soil fractions were: humic acids, 30.7 ppm; humin, 6.97 ppm; fulvic acids, 5.95 ppm, and inorganic fractions 0.526 ppm(11). Aerobic biomineralization over 28 days in the soil ranged from 1.21% (humic acid) to 4.98% (fulvic acids and 2.18% overall, compared with 9.04% for the free chemical(11). Similarly, in a standard photomineralization test in which the test substance is put on silica gel and illuminated for 17 hours, 14CO2 formation ranged from 0.08% (humic acid) to 1.43% (fulvic acid) and 1.39% overall, compared with 26.06% for the free chemical(11).

AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 96-1,530(2,3), indicate that 4-chloroaniline may be expected to adsorb to suspended solids and sediment(SRC). A Koc of 5,550 was reported for 4-chloroaniline binding to colloidal organic matter in ground water(4). Volatilization from water surfaces is expected(5) based upon an estimated Henry's Law constant of 3.1X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.071 mm Hg(6), and water solubility, 3.9 g/L(7). Using this Henry's Law constant and an estimation method(5), volatilization half-lives for a model river and model lake are 36 and 260 days, respectively(SRC). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(8,9), and volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The pKa of 4-chloroaniline is 3.98(10), indicating that this compound will primarily exist in its nonionic form in the environment. According to a classification scheme(11), BCF values ranging from 0.8 to <20(12-14), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 4-Chloroaniline is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(15). The half-life of 4-chloroaniline under illumination conditions typifying those for US surface waters in summer is 0.4 hour(16). When (14)C labeled 4-chloroaniline was added to an experimental pond (ca. 50 ppb over 6-8 wk), the (14)C label disappeared from the water in two phases with half-lives of about 3 and 11 days(17). It was assumed that the initial loss results from volatilization(17). Radioactivity could be found in some fauna species and sediment 3 yr after application (17). In estuarine water, photolysis was an important loss process for 4-chloroaniline, but no biodegradation occurred in 3 days(18). The estimated half-lives of 4-chloroaniline in river water and ground water based on monitoring data are 0.3-3 day and 30-300 day, respectively(19). Photolysis half-lives of 1.10 and 1.30 hours in distilled and Isar river water were reported for 4-chloroaniline (2-5 mg/L) when exposed to sunlight; photoproducts were 4-aminophenol and polymers(20).

Of the 3 compounds, kepone, 4-chloroaniline, and aldrin, persistence of kepone residues in soil was highest. Decrease in kepone and 4-chloroaniline in soil occurred in about 2 stages, a fast one lasting in the case of 4-chloroaniline 0.5 yr and a subsequent slow one. In another experiment, these compounds were detectable in soil, ground waters and plants 3 yr after application.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-chloroaniline, which has a vapor pressure of 0.071 mm Hg at 25 °C((2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 4-chloroaniline is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 9 hours(SRC), calculated from its rate constant of 4.3X10-11 cu cm/molecule-sec at 25 °C(3). 4-chloroaniline was found to undergo photolysis in aqueous solution when irradiated by sunlight(5,6); it may also be susceptible to direct photolysis by sunlight in air(SRC).

THE METABOLISM OF 4-CHLOROANILINE BY ISOLATED CULTURES OF THE SOIL FUNGUS FUSARIUM OXYSPORUM SCHLECHT WAS STUDIED. 2-AMINO-5-CHLOROPHENOL WAS POSITIVELY IDENTIFIED AS METABOLITE OF 4-CHLOROANILINE IN THE ISOLATED SOIL FUNGUS CULTURES.

A Pseudomonas species, isolated from soil, was grown aerobically on 4-chloroaniline as the only carbon and nitrogen source with generation time of 15 hr. Balance studied with (14)C-ring-labeled 4-chloroaniline revealed that 64% of the carbon of 4-chloroaniline was released as CO2 and 14% was associated with the biomass.

AEROBIC: The results of biodegradability screening studies for 4-chloroaniline are conflicting with results ranging from no degradation to rapid degradation using soil, sewage, activated sludge and fresh water inocula(SRC). The most frequently reported results are that 4-chloroaniline biodegrades rather slowly with acclimation(1-5). The reason for the conflicting results may be due to toxicity of metabolic intermediates(1), differences in concentrations and inocula used, sensitivity of 4-chloroaniline to chemical oxidation, and lack of sufficient acclimation(SRC). Some results are summarized as follows. 4-Chloroaniline degraded 28% after 5 days using the GSF Biodegradation Test(2). In a Modified OECD Screening test, 10% and 18% degradation in 28 days of 4-chloroaniline was observed(2,5). Using a Closed Bottle Test, no degradation of 4-chloroaniline was observed in 28-30 days(2,3). 4-Chloroaniline was degraded 97% after 10-16 days including an 8 day lag period in a test using a simulated activated sludge procedure(3). In a test using adapted activated sludge (20-day acclimation), 96.5% removal based upon dissolved organic carbon was observed after 5 days(4). In the Zahn-Wellens test, 97% dissolved organic carbon was removed in 14 days(6).

AEROBIC: In a river die-away test, 4-chloroaniline (10 ppm) degraded slowly in Nile River water over a period of 2 months but on redose increasingly larger concentrations of the chemical were degraded in shorter and shorter times so that on the 8th redose 100 ppm was degraded in a few days(6). No 4-chloroaniline (18.8 and 0.48 mg/L) degraded in 103 days at 15 °C in a shake flask screening test using natural sea water(5). However, in simulation tests performed at the same temperature and with the same sea water, but at very low concns, 1 and 4 ug/L, first order rate constants (half-lives) of 0.0073/day (95 day) and 0.0076/day (91 day), respectively were obtained(5). Several studies were performed where labeled 4-chloroaniline was incubated with soil(3,4,7). In one study, 12-17% mineralization occurred in 16 weeks with the maximum rate of degradation occurring between 1 and 3 weeks(7). 86% of the labeled residue was present as unextractable material bound to the soil and 1-4% of the residues were extractable(7). 14C-Labeled 4-chloroaniline was added to autoclaved and nonautoclaved soils and incubated for 6 weeks(4). No CO2 evolution was observed in the sample using autoclaved soil(4). In the nonautoclaved samples, CO2 could be detected at 7.5% of the originally applied radioactivity for 4-chloroaniline(4). In a third study, 14-C labeled 4-chloroaniline was found to degrade 8.5 and 9.0% to CO2 after 16 weeks of incubation in two soils(3). It has been suggested that the binding of the chloroaniline to soil may extend its life in soil to 10 years(1). During composting with refuse, 14% of the 4-chloroaniline was metabolized in 21 days(2).

For more Environmental Biodegradation (Complete) data for 4-CHLOROANILINE (6 total), please visit the HSDB record page.

The rate constant for the vapor-phase reaction of 4-chloroaniline with photochemically-produced hydroxyl radicals is 4.30X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). 4-Chloroaniline is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). 4-Chloroaniline absorbs light >290 nm(4). On irradiation with light >290 nm in air-saturated water 4-chloroaniline photolyzes to form 4-chloronitrobenzene and 4-chloronitrosobenzene(5). 4-Chloroaniline completely disappears within 6 hours and dark purple condensation products are subsequently formed(5). The half-life of 4-chloroaniline under illumination conditions typifying those for US surface waters in summer is 0.4 hr(6). This rate is not increased by the presence of algae in the water(6). 28% of the 4-chloroaniline adsorbed on silica gel was photomineralized to CO2 in 17 hr(7). The half-life of 4-chloroaniline in a photoreactor exposed to light > 290 nm was decreased by a factor of 2 (from 5 min) when riboflavin was present(8). 4-Chloroaniline also reacts rapidly with manganese dioxide, which may be present in natural water and soil, resulting in the formation of azo compounds(9). In one experiment (pH 4, concn MnO2 5X10-3 mol/L), the initial rate of reaction at pH 4 was 1.1X10-3 mol/L-min(9). Sunlight did not enhance the rate of reaction(10). Photolysis half-lives of 1.10 and 1.30 hours in distilled and Isar river water were reported for 4-chloroaniline (2-5 mg/L) when exposed to sunlight; photoproducts were 4-aminophenol and polymers(11).

The average BCFs in the whole body of carp exposed to 4-chloroaniline in flow-through experiments (25 °C, 12 L/hr) for 24 to 336 hr at high (10.4 ug/L) and low (0.30 ug/L) exposure levels were 0.8 and 1.7, respectively(3). Excretion was rapid with depuration rates and half-lives of 0.16/hr and 4.3 hr, respectively(3). Therefore, 4-chloroaniline should not bioconcentrate in fish. Uptake was rapid in static tests (0.20 umol/L, 26 °C) on zebrafish and a BCF of 8.1 was obtained for 24 hr exposure(4). Elimination was best described by a two compartment first order model(4). After 53 hr of depuration, the concn of 4-chloroaniline in the zebrafish declined to 12.0% of the steady state value. The log BCF in Golden orfe was <1.30 for 3 day exposure(1). The 24-hr log BCF in green alga was 3.08 (dry wt basis(2)) and 2.42 (wt weight basis(1)). A BCF of 13.4 was reported for guppy (Poecilia reticulata)(5). According to a classification scheme(6), these BCF values suggest the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc for 5 Belgium soils ranged from 230-469(1). The adsorption isotherm was not linear and the exponent in the Freundlich adsorption isotherm averaged 0.70(1). The Koc for 5 German soils ranged from 96 to 1,530 with the Freundlich exponent ranging from 0.92 to 1.23(2). From adsorption studies on three soils with radically different organic carbon and clay contents, it was shown that the percent (14)C labeled 4-choloroaniline that was bound increased with the organic carbon content of the soil and decreased with its clay content(3). Stronger binding at low concns, particularly with the soil of low organic carbon content, suggests that there are a limited number of available binding sites on the soil(3). At the lower concn (5ppm), percent binding ranged from 46-78%(3). The Koc to colloidal organic matter in ground water was high, 5,550, suggesting that adsorption onto this microparticulate matter could effectively increase the solubility and leaching of 4-chloroaniline into landfill groundwater(4). According to a classification scheme(5), Koc values between 50-150 suggest that 4-chloroaniline is expected to have high mobility in soil, Koc values >500 to >5000 suggest 4-chloroaniline is expected to have low to no mobility in soil. Aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(7,8), suggesting that mobility may be much lower in some soils(SRC). Adsorption of 4-chloroaniline by 5 soils was studied in the lab; adsorption decreased with the depth of the soil sample, due to decreased organic carbon(6). Adsorption coefficients of 4-chloroaniline and 4 other organic compounds for organic and inorganic materials and natural soils were determined(2). With few exceptions, the organic constituents of the soils were mainly responsible for their adsorption properties(2). Cellulose appeared to be a well-suited model adsorbent for simulating the relative adsorption behavior of the chemicals(2). The pKa of 4-chloroaniline is 3.98(9), indicating that this compound will primarily exist in its nonionic form in the environment.

Aromatic amines form covalent bonds with humic materials, adding to model quinoidal structures such as are found in humic materials, followed by slow oxidation to nitrogen-substituted quinoidal rings(1,6). Condensation with hydroquinones to form phenoxazines is another mechanism for incorporating anilines into humic substances(6). The reaction half-life of 4-chloroaniline with one test humic constituent was 13 min(1). Hybrid oligomers were formed between 4-chloroanline and carboxyphenolic humus constituents(2,5). These oxidative coupling reactions are mediated by biotic and abiotic catalysts, such as microbial and plant enzymes, inorganic chemicals, clay and soil extracts with MnO2 and enzymes having the strongest catalytic effect(5,6). This type of crosscoupling product would explain the fast, strong, and irreversible binding of anilines to soil(3). After 1 year, 10-20% of (14)C residues remained in the upper 10 cm of soil(3). Another field experiment using (14)C resulted in 30% of the label remaining where it was applied, while little was found at lower depths or in leachate(4).

ADSORBED 4-CHLOROANILINE DESORPTION RATES FROM DIFFERENT SOILS INTO WATER WERE 11.9% TO 68.3%; % REPLACEABLE BY 3,4-DICHLOROANILINE WAS 17.9% TO 100%, INDICATING WEAKLY SORBED FRACTION. PROLONGED SOIL RESIDENCE OF 4-CHLOROANILINE GIVES CHEMICAL BONDING, INSEPARABLE FROM SOIL.

Release of tightly complexed 4-chloroaniline from treated soil humic acids and whole soils by pyrolysis in atmosphere of helium was studied. Pyrolysis of soil humic acids containing tightly complexed 4-chloroaniline resulted in release of approx 54% of the radioactivity with approx 5% detected via radioassay or gas-liq chromatography as intact 4-chloroaniline. Three soils of varying organic matter and clay concentrations complexed 10% of applied 4-chloroaniline; extractable radioactivity incr and tightly complexed 4-chloroaniline decreased as organic matter concn decreased and clay concn increased. The quantity of radioactivity released by pyrolysis was greatest for soils with low organic matter and high clay contents; 22-73% of the radioactivity could be released with 3-16% extractable into benzene from basified pyrolyzate, the amt depending on the nature of the soil, the type of pyrolysis probe, and the concn of the applied 4-chloroaniline.

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P024, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids.

PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/

For more Disposal Methods (Complete) data for 4-CHLOROANILINE (7 total), please visit the HSDB record page.

/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Health: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Chloroanilines, liquid; Chloroanilines, solid/

/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Chloroanilines, liquid; Chloroanilines, solid/

/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. /Chloroanilines, liquid; Chloroanilines, solid/

/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Chloroanilines, liquid; Chloroanilines, solid/

For more DOT Emergency Guidelines (Complete) data for 4-CHLOROANILINE (8 total), please visit the HSDB record page.

IMO 6.1; Chloroanilines, liquid or solid

UN 2019; Chloroanilines, liquid

UN 2018; Chloroanilines, solid

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./

The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.

The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/

Do not transport with food and feedstuffs.

Symbol: T, N; R: 45-23/24/25-43-50/53; S: 53-45-60-61; Note: E

UN Hazard Class: 6.1; UN Pack Group: II