2,4-dichloroaniline

H301 (96.4%): Toxic if swallowed [Danger Acute toxicity, oral]

H311 (98.2%): Toxic in contact with skin [Danger Acute toxicity, dermal]

H331 (98.2%): Toxic if inhaled [Danger Acute toxicity, inhalation]

H373 (94.5%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

H400 (85.5%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (94.5%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

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

Aggregated GHS information provided per 55 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.

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]

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

H302: Harmful if swallowed [Warning Acute toxicity, oral]

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]

P260, P264, P270, P301+P317, P308+P316, P319, P321, P330, P405, and P501 (click each P-code to see the statement)

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]

H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]

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

P260, P261, P262, P264, P264+P265, P270, P271, P272, P280, P301+P316, P302+P352, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P333+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Fresh air, rest. Artificial respiration may be needed. 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. Give one or two glasses of water to drink. 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)

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

If material on fire or involved in fire: Use dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. use water in flooding quantities as fog. /Dichloroaniline/

Personnel protection: ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Dichloroaniline/

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (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: chemical protection suit including self-contained breathing apparatus. Remove all ignition sources. Do NOT wash away into sewer. Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

... ANILINE SHOULD BE REACTED IN CLOSED VESSELS AS FAR AS POSSIBLE. IN FACTORIES VENTILATION SHOULD BE SUFFICIENT TO KEEP ATMOSPHERIC ANILINE CONTENT WELL BELOW PERMITTED LEVEL. /ANILINE/

Eating and smoking should not be allowed in areas where liquid aniline is handled, processed, or stored. /Aniline/

Clothing which becomes soaked with aniline should be promptly removed. /Aniline/

For more Preventive Measures (Complete) data for 2,4-DICHLOROANILINE (9 total), please visit the HSDB record page.

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere, and store it at refrigerated temperatures. (NTP, 1992)

Separated from strong oxidants and food and feedstuffs.

STORE IN A COOL, DRY, WELL-VENTILATED LOCATION. SEPARATE FROM ACIDS, OXIDIZING MATERIALS, & COMBUSTIBLES. /DICHLOROANILINES/

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is mildly irritating to the skin. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. Exposure could cause death. The effects may be delayed. Medical observation is indicated.

The substance may have effects on the blood. This may result in the formation of methaemoglobin.

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

POSSIBLE EXPOSURE TO HIGHER CONCN (PIPE BREAKAGE, SPLASHING, CLEANING OR REPAIR OF STORAGE TANKS) NECESSITATES USE OF SAFETY GOGGLES, GAS MASK, APRON, & RUBBER GLOVES. /ANILINE/

RESPIRATOR FOR ORGANIC VAPORS, SPLASHPROOF GOGGLES ... /&/ BOOTS. /ANILINE/

Respiratory protection from aniline is as follows: vapor concentration of 100 ppm or less: a chemical cartridge respirator with a full facepiece and an organic vapor cartridge(s) or a gas mask with a chin-style front or back-mounted organic vapor canister or any supplied-air respirator with a full facepiece, helmet or hood, or any self-contained breathing apparatus with a full facepiece; greater than 100 ppm or entry and escape from unknown concentrations: self-contained breathing apparatus with a full facepiece operated in pressure demand or other positive pressure mode or a combination respirator which includes a type C supplied-air respirator with a full facepiece operated in pressure-demand or other positive pressure or continuous-flow mode and an auxiliary self-contained breathing apparatus operated in pressure-demand or other positive pressure mode; escape: any gas mask providing protection against organic vapors or any self-contained breathing apparatus. /Aniline/

Butyl rubber protective clothing ... . /Aniline/

Wear special protective clothing and positive pressure self-contained breathing apparatus. /Dichloroanilines/

NO open flames.

PREVENT DISPERSION OF DUST!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles or face shield.

Do not eat, drink, or smoke during work. Wash hands before eating.

2,4-dichloroaniline appears as beige crystals. (NTP, 1992)

Other Solid; Large Crystals

COLOURLESS CRYSTALS WITH CHARACTERISTIC ODOUR.

PRISMS FROM ACETONE; NEEDLES FROM DILUTED ALCOHOL OR PETROLEUM ETHER

473 °F at 760 mmHg (NTP, 1992)

245 °C AT 760 mm Hg

145 to 147 °F (NTP, 1992)

63-64 °C

less than 1 mg/mL at 73 °F (NTP, 1992)

Slightly soluble in water, alcohol, and ether.

Solubility in water: none

1.567 at 68 °F (NTP, 1992) - Denser than water; will sink

1.567 @ 20 °C

1.57 g/cm³

Relative vapor density (air = 1): 5.6

Vapor pressure, Pa at 25 °C:

log Kow= 2.91

When heated to decomposition it emits toxic vapors of nitrogen oxides and /hydrogen chloride/.

370 °C. Decomposes on burning. This produces toxic fumes including nitrogen oxides and hydrogen chloride (see ICSC 0163).

pKa= 2.00 (conjugate acid)

13C nuclear magnetic resonance spectrum

Chemical shift

Nuclear quadrupole resonance spectroscopy

Quadrupole coupling

Spin-spin coupling constant

This chemical may be sensitive to exposure to air. Insoluble in water.

Aryl Halides

Amines, Aromatic

2,4-DICHLOROANILINE is incompatible with acids, acid chlorides, acid anhydrides and oxidizing agents. (NTP, 1992)

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

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

MAY BE ABSORBED! Redness. Further see Inhalation.

Redness. Pain.

Abdominal pain. Further see Inhalation.

LD50 Rat oral 1600 mg/kg

LD50 Rat ip 400 mg/kg

LD50 Mouse oral 400 mg/kg

LD50 Mouse ip 400 mg/kg

Basic treatment: Establish patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aniline and related compounds/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W TKO /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation. /Aniline and related compounds/

TWENTY-ONE HALO-SUBSTITUTED ANILINES WERE COMPARED WITH ANILINE FOR THEIR ABILITY TO STIMULATE METHEMOGLOBIN FORMATION IN CATS. HALO SUBSTITUTIONS IN THE 4-POSITION INCREASED THE ACTIVITY OF ANILINE, WHILE SUBSTITUTIONS IN THE 2 AND 3 POSITIONS DID NOT CHANGE OR REDUCE THE ACTIVITY. POLYHALO SUBSTITUENTS (SUCH AS 2,6-DICHLOROANILINE) REDUCED THE ACTIVITY COMPARED TO ANILINE. /DICHLOROANILINES/

IN GUELPH LOAM, 2,4-DICHLOROANILINE, AT CONCN OF 5-100 UG/G SOIL, WAS INHIBITORY AGAINST THE OXIDN OF THE NITROGEN OF AMMONIA TO NITRITE NITROGEN BY NITROSOMONAS, BUT NOT NITRITE NITROGEN TO NITRATE. THE DICHLOROANILINES SHOWED INCREASED TOXICITY AGAINST NITROSOMONAS.

Ten substances were tested to compare two methods that can be used in chronic toxicity studies with the cladoceran Daphnia magna. In semistatic experiments with cohorts (life-table studies) survival appeared to be a dominant factor in exponential population growth. Specific inhibition of reproduction as a result of toxic stress was observed in tests with 2,4-dichloroaniline.

Dichloroaniline produces methemoglobinemia in rats & mice. /Dichloroaniline/

Like other chloroanilines, the primary toxic effect of 2,4-, 2,5-, and 3,4-dichloroaniline is methemoglobin formation, which is attributed to the intermediate formation of hydroxylated metabolites. Acute intoxication is indicated by the symptoms of methemoglobinemia (cyanosis, fatigue, dyspnoea, muscle weakness). Judging by doses which had an effect in animal experiments, dichloroanilines showed moderate acute toxicity. After occlusive application to experimental animals, 2,4-dichloroaniline was moderately irritant on skin. 3,4-dichloroaniline was not irritant on rabbit skin, and the results for irritancy in the eye varied from not irritant to irritant. The 2,5-isomer was not irritant on rabbit skin, but caused irritant effects in the eye; the effects were severe and not completely reversible. The hyperkeratogenous and acnegenic effects documented in the literature were attributed to 3,3',4,4'-tetrachloroazobenzene and 3,3',4,4'-tetrachloroazoxybenzene, impurities formerly present in industrial 3,4-dichloroaniline. 3,4-dichloroaniline had no photoallergic effect on the mouse. The maximization test on the guinea pig revealed that 3,4- and 2,5-dichloroaniline had skin sensitizing potential. There are no data on the sensitizing effect of the 2,4-isomer. Like after acute application, hematological changes become evident after repeated application of dichloroanilines. An increase in both haemoglobin break-down and hematopoiesis was observed in the rat after subacute oral administration of 2,5-dichloroaniline at doses of 150 mg/kg body weight and above. The NOEL was 30 mg/kg body weight per day. After repeated administration of 3,4-dichloroaniline by inhalation (6 h/d, 5 d/w over 2 weeks), there was evidence of slight methemoglobin formation at an exposure concentration of 10 mg/cu m and above, histopathological changes in the spleen (hemosiderin deposits) at 45 mg/cu m and above and extramedullary hematopoiesis at 200 mg/cu m. Most of the mutagenicity tests carried out did not indicate any genotoxic effects of dichloroanilines. None of the isomers considered here was mutagenic in the numerous Ames tests, either with or without metabolic activation, or when Norharman was added. 2,5-dichloroaniline did not cause any chromosomal damage to V79 cells in the chromosome aberration test, it was not mutagenic in E. coli WP2uvrA, and it did not damage DNA in the UDS test on hepatic cells. Similarly, 3,4-dichloroaniline did not have any mutagenic activity in mammalian cells in the HGPRT test. A positive result was recorded in the fungus Aspergillus nidulans and in the pol A1- -test on E. coli. Several UDS tests on hepatic cells showed that 3,4-dichloroaniline did not damage DNA; one UDS test recorded a weak positive result. There was no increase in the frequency of sister chromatid exchanges in lymphocytes without metabolic activation, but an increase was observed when S9 mix was added. There was no indication of chromosomal damage in Allium cepa, in mammalian cells during the chromosome aberration test and in vivo in the mouse during the micronucleus test for 3,4-dichloroaniline. There are no studies on carcinogenicity. 3,4-dichloroaniline was not teratogenic inanimal experiments and was embryotoxic only at distinctly maternotoxic doses.

LC50 Poecilia reticulata (guppy) 11.7 ppm/14 days /Conditions of bioassay not specified/

The substance is toxic to aquatic organisms.

2,4-Dichloroaniline's production and use as an intermediate in the production of dye stuffs, pesticides or pharmaceuticals may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 1.5X10-2 mm Hg at 25 °C indicates 2,4-dichloroaniline will exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,4-dichloroaniline 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 42 hours. 2,4-Dichloroaniline may undergo photolysis since it absorbs environmental UV light (>290 nm). If released to soil, 2,4-dichloroaniline is expected to have low mobility based upon a Koc of 525. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 1.6X10-6 atm-cu m/mole. If released into water, 2,4-dichloroaniline is expected to adsorb to suspended solids and sediment in the water column based upon the estimated Koc. Photolysis rate constants of 0.071/hr and 0.033/hr in water were determined for summer and winter conditions, respectively, corresponding to respective half-lives of 10 and 21 hrs. No microbial degradation of 2,4-dichloroaniline occurred during short term incubations (up to 3 days) in die-away tests using an estuarine water from the Skidaway River in Georgia. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 30 and 219 days, respectively. However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. An BCF of 94.7 suggests bioconcentration in aquatic organisms is moderate. Occupational exposure to 2,4-dichloroaniline may occur through inhalation and dermal contact with this compound at workplaces where 2,4-dichloroaniline is produced or used. The general population may be exposed to 2,4-dichloroaniline via inhalation of ambient air, ingestion of drinking water, dermal contact with this compound in products containing certain dyes, pesticides, and plastics made from 2,4-dichloroaniline. (SRC)

2,4-Dichloroaniline's production and use as an intermediate in the production of dyestuffs, pesticides or pharmaceuticals(1,2) may result in its release to the environment through various waste streams(SRC). Aromatic amines (such as 2,4-dichloroaniline) are introduced into the environment directly as industrial effluents and indirectly as transformation products(1). Dichloroanilines arise from corresponding nitrodichloroanilines when the latter are metabolized by fungi(3).

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 525(2), indicates that 2,4-dichloroaniline is expected to have low mobility in soil(SRC). Volatilization of 2,4-dichloroaniline from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 2,4-Dichloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.5X10-2 mm Hg(SRC), determined from a fragment constant method(4). Adsorption to soil is expected to attenuate volatilization(SRC). In shake-flask screening tests using soil microbes adapted to isopropyl N-phenylcarbamate, ring degradation of 86-100% was observed for 2,4-dichloroaniline over incubation periods of 8-22 days(5).

AQUATIC FATE: Based on a classification scheme(1),a Koc value of 525(2), indicates that 2,4-dichloroaniline is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.6X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Volatilization half-lives for a model river and model lake are 30 and 219 days, respectively(SRC), using an estimation method(3). However, this model underestimates the volatilization half-life of 2,4-dichloroaniline since it does not take into account the effects of adsorption. The Koc of 525(2) suggests that volatilization could be attenuated by adsorption to suspended solids and sediments in water(SRC). This is apparent from the results of two EXAMS model runs, one in which the effect of adsorption was considered (half-life = 842 days in a model pond) and one in which adsorption was ignored (half-life = 317 days in a model pond)(5). A BCF of 94.7(6), suggests bioconcentration in aquatic organisms is moderate. The photochemical degradation process of 2,4-dichloroaniline in aquatic environments was linear according to the first-order decay rate(7). Photolysis rate constants of 0.071/hr and 0.033/hr in water were determined for summer and winter conditions, respectively, corresponding to respective half-lives of 10 and 21 hrs(8). No microbial degradation of 2,4-dichloroaniline occurred during short term incubations (up to 3 days) in die-away tests using an estuarine water from the Skidaway River in Georgia(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semi-volatile organic compounds in the atmosphere(1), 2,4-dichloroaniline, which has an estimated vapor pressure of 1.5X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,4-dichloroaniline 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 42 hours(SRC) from its estimated rate constant of 9.2X10-12 cu cm/molecule sec(3). 2,4-Dichloroaniline absorbs light in the environmental spectrum (>290 nm) and may undergo direct photolysis(4,5); half-lives in water ranged from 10-21 hours(5).

AEROBIC: Biodegradation of 2,4-dichloroaniline was not observed in freshwater samples if no sunlight was present. Photolysis of 2,4-dichloroaniline increased bacterial numbers presumably due to the utilization of the degradation products formed(1). Incubation of 2,4-dichloroaniline in covered beakers containing a sandy loam soil for 14 days yielded the azo compound 2,2',4,4'-tetrachloroazobenzene(2). No azo compounds were detected in control incubations using sterilized soil. Products other than azo compounds were not isolated or analyzed for(2). In shake-flask screening tests using soil microbes adapted to isopropyl N-phenylcarbamate, ring degradation of 86-100% was observed for 2,4-dichloroaniline over incubation periods of 8-22 days(3). No microbial degradation of 2,4-dichloroaniline occurred during short term incubations (up to 3 days) in die-away tests using an estuarine water from the Skidaway River in Georgia(4).

ANAEROBIC: In unacclimated sediment slurries spiked with 10 mg/l of 2,4-dichloroaniline, dechlorination to the monochlorophenol intermediates began after a lag period of 4 weeks and was complete within the following 10 days. In acclimated sediments, dechlorination to monochlorophenol intermediates began immediately and was complete in 9 days. 2,4-Dichloroaniline was reductively dechlorinated in dichlorophenol acclimated sediments without lag(1).

The rate constant for the vapor-phase reaction of 2,4-dichloroaniline with photochemically-produced hydroxyl radicals has been estimated as 9.2X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 42 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1). 2,4-Dichloroaniline is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3); however, it may directly photolyze due to absorption in the environmental UV spectrum(4). Photochemical degradation process of 2,4-dichloroaniline in aquatic environments was linear according to the first-order decay rate(4). Freshwater samples from the Mississippi River were incubated with 2,4-dichloroaniline (10 mg/l) at 28 °C for 3 hours in midday sunlight. Total bacterial numbers in the photo-exposure groups increased dramatically, pressumably as a result of bacterial utilization of the degradation products that were produced during photochemical and microbial degradation. There was no 2,4-dichloroaniline degradation in the control group kept in darkness(4). Photolysis rate constants of 0.071/hr and 0.033/hr in distilled water were determined for summer and winter conditions, respectively, corresponding to respective half-lives of 10 and 21 hrs(5).

A BCF of 94.7 was experimentally determined for 2,4-dichloroaniline under static conditions in a closed basin with 60 male zebra fish and 5000 ml of carbon filtered tap water(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

The Koc of 2,4-dichloroaniline is 525(1). According to a classification scheme(2), this Koc value suggests that 2,4-dichloroaniline will have low mobility in soil. A Koc of 3930 was measured at pH 6.5 using a colloidal-sized fraction of dissolved organic carbon isolated from groundwater monitoring wells(3). In soil column leaching studies simulating waste leaching from landfill sites, 2,4-dichloroaniline exhibited moderate leaching when leached in combination with leachate from domestic landfill sites(4). Aromatic amines (such as various chloro- and dichloroaniline isomers) have been observed to undergo rapid and reversible covalent bonding with humic materials in aqueous solution. The initial bonding reaction is followed by a slower and much less reversible reaction believed to represent the addition of the amine to quinoidal structures in humic material followed by oxidation of the product to give an amino-substituted quinone(5).

The Henry's Law constant for 2,4-dichloroaniline is estimated as 1.6X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,4-dichloroaniline is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as approximately 711 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as approximately 219 days(SRC). However, the volatilization half-life does not take into account the effects of adsorption. A Koc value of 525(3) suggests that volatilization could be attenuated by adsorption to suspended solids and sediments in water(SRC). This is apparent from the results of two EXAMS model runs, one in which the effect of adsorption was considered, yielding an estimated half-life of 842 days in a model pond 2 m deep, and one in which the effect of adsorption was ignored, yielding an estimated half-life of 317 days in a model pond 2 m deep(4). 2,4-Dichloroaniline's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). 2,4-Dichloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.5X10-2 mm Hg(SRC), determined from a fragment constant method(5).

SURFACE WATER: 2,4-Dichloroaniline was detected at 7 ng/l (minimum) and 26 ng/l (max) upstream of Hamburg, Germany and at 5.3 ng/l (minimum) and 21 ng/l (max) downstream of Hamburg(1). In 1979, 92 surface water samples were collected at 3 sites on the Rhine River and 2 sites on the Meuse River in the Netherlands and Belgium and analyzed for aromatic amines(2). 2,4-Dichloroaniline was detected in 7 of 46 samples at Lobith (Rhine R; 0.76 ppb max, 0.02 ppb mean), 3 of 12 samples at Boven Merwede (Rhine River; 0.15 ppb max, 0.02 ppb mean), 4 of 13 samples at Ijssel (Rhine River; 0.08 ppb max, 0.02 ppb mean), 0 of 9 samples at Eijsden (Meuse River), and 1 of 12 samples at Lith (Meuse Rivers; 0.32 ppb max, 0.03 ppb mean)(2).

2,4-Dichloroaniline was found to occur only once in over 4000 samples of waste waters from 46 industrial categories(1). It was detected in the wastewater effluent generated from the organic chemicals industry, concentration not specified(1). 2,4-Dichloroanilne was detected in sewage sludge from Brandenburg, Germany during the summer at 0.8 mg/kg (median) and 2 mg/kg (max) while during winter it was detected at 0.2 mg/kg (median) and 0.6 mg/kg (max) in sewer sludge dry matter(2).

Occupational exposure to 2,4-dichloroaniline may occur through inhalation and dermal contact with this compound at workplaces where 2,4-dichloroaniline is produced or used(SRC). The general population may be exposed to 2,4-dichloroaniline via ingestion of drinking water(1), dermal contact with this compound in products containing certain dyes, pesticides, and plastics made from 2,4-dichloroaniline(2).

LC50 Poecilia reticulata (guppy) 11.7 ppm/14 days /Conditions of bioassay not specified/

The substance is toxic to aquatic organisms.

2,4-Dichloroaniline's production and use as an intermediate in the production of dye stuffs, pesticides or pharmaceuticals may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 1.5X10-2 mm Hg at 25 °C indicates 2,4-dichloroaniline will exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,4-dichloroaniline 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 42 hours. 2,4-Dichloroaniline may undergo photolysis since it absorbs environmental UV light (>290 nm). If released to soil, 2,4-dichloroaniline is expected to have low mobility based upon a Koc of 525. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 1.6X10-6 atm-cu m/mole. If released into water, 2,4-dichloroaniline is expected to adsorb to suspended solids and sediment in the water column based upon the estimated Koc. Photolysis rate constants of 0.071/hr and 0.033/hr in water were determined for summer and winter conditions, respectively, corresponding to respective half-lives of 10 and 21 hrs. No microbial degradation of 2,4-dichloroaniline occurred during short term incubations (up to 3 days) in die-away tests using an estuarine water from the Skidaway River in Georgia. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 30 and 219 days, respectively. However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. An BCF of 94.7 suggests bioconcentration in aquatic organisms is moderate. Occupational exposure to 2,4-dichloroaniline may occur through inhalation and dermal contact with this compound at workplaces where 2,4-dichloroaniline is produced or used. The general population may be exposed to 2,4-dichloroaniline via inhalation of ambient air, ingestion of drinking water, dermal contact with this compound in products containing certain dyes, pesticides, and plastics made from 2,4-dichloroaniline. (SRC)

2,4-Dichloroaniline's production and use as an intermediate in the production of dyestuffs, pesticides or pharmaceuticals(1,2) may result in its release to the environment through various waste streams(SRC). Aromatic amines (such as 2,4-dichloroaniline) are introduced into the environment directly as industrial effluents and indirectly as transformation products(1). Dichloroanilines arise from corresponding nitrodichloroanilines when the latter are metabolized by fungi(3).

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 525(2), indicates that 2,4-dichloroaniline is expected to have low mobility in soil(SRC). Volatilization of 2,4-dichloroaniline from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 2,4-Dichloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.5X10-2 mm Hg(SRC), determined from a fragment constant method(4). Adsorption to soil is expected to attenuate volatilization(SRC). In shake-flask screening tests using soil microbes adapted to isopropyl N-phenylcarbamate, ring degradation of 86-100% was observed for 2,4-dichloroaniline over incubation periods of 8-22 days(5).

AQUATIC FATE: Based on a classification scheme(1),a Koc value of 525(2), indicates that 2,4-dichloroaniline is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.6X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Volatilization half-lives for a model river and model lake are 30 and 219 days, respectively(SRC), using an estimation method(3). However, this model underestimates the volatilization half-life of 2,4-dichloroaniline since it does not take into account the effects of adsorption. The Koc of 525(2) suggests that volatilization could be attenuated by adsorption to suspended solids and sediments in water(SRC). This is apparent from the results of two EXAMS model runs, one in which the effect of adsorption was considered (half-life = 842 days in a model pond) and one in which adsorption was ignored (half-life = 317 days in a model pond)(5). A BCF of 94.7(6), suggests bioconcentration in aquatic organisms is moderate. The photochemical degradation process of 2,4-dichloroaniline in aquatic environments was linear according to the first-order decay rate(7). Photolysis rate constants of 0.071/hr and 0.033/hr in water were determined for summer and winter conditions, respectively, corresponding to respective half-lives of 10 and 21 hrs(8). No microbial degradation of 2,4-dichloroaniline occurred during short term incubations (up to 3 days) in die-away tests using an estuarine water from the Skidaway River in Georgia(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semi-volatile organic compounds in the atmosphere(1), 2,4-dichloroaniline, which has an estimated vapor pressure of 1.5X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,4-dichloroaniline 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 42 hours(SRC) from its estimated rate constant of 9.2X10-12 cu cm/molecule sec(3). 2,4-Dichloroaniline absorbs light in the environmental spectrum (>290 nm) and may undergo direct photolysis(4,5); half-lives in water ranged from 10-21 hours(5).

AEROBIC: Biodegradation of 2,4-dichloroaniline was not observed in freshwater samples if no sunlight was present. Photolysis of 2,4-dichloroaniline increased bacterial numbers presumably due to the utilization of the degradation products formed(1). Incubation of 2,4-dichloroaniline in covered beakers containing a sandy loam soil for 14 days yielded the azo compound 2,2',4,4'-tetrachloroazobenzene(2). No azo compounds were detected in control incubations using sterilized soil. Products other than azo compounds were not isolated or analyzed for(2). In shake-flask screening tests using soil microbes adapted to isopropyl N-phenylcarbamate, ring degradation of 86-100% was observed for 2,4-dichloroaniline over incubation periods of 8-22 days(3). No microbial degradation of 2,4-dichloroaniline occurred during short term incubations (up to 3 days) in die-away tests using an estuarine water from the Skidaway River in Georgia(4).

ANAEROBIC: In unacclimated sediment slurries spiked with 10 mg/l of 2,4-dichloroaniline, dechlorination to the monochlorophenol intermediates began after a lag period of 4 weeks and was complete within the following 10 days. In acclimated sediments, dechlorination to monochlorophenol intermediates began immediately and was complete in 9 days. 2,4-Dichloroaniline was reductively dechlorinated in dichlorophenol acclimated sediments without lag(1).

The rate constant for the vapor-phase reaction of 2,4-dichloroaniline with photochemically-produced hydroxyl radicals has been estimated as 9.2X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 42 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1). 2,4-Dichloroaniline is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3); however, it may directly photolyze due to absorption in the environmental UV spectrum(4). Photochemical degradation process of 2,4-dichloroaniline in aquatic environments was linear according to the first-order decay rate(4). Freshwater samples from the Mississippi River were incubated with 2,4-dichloroaniline (10 mg/l) at 28 °C for 3 hours in midday sunlight. Total bacterial numbers in the photo-exposure groups increased dramatically, pressumably as a result of bacterial utilization of the degradation products that were produced during photochemical and microbial degradation. There was no 2,4-dichloroaniline degradation in the control group kept in darkness(4). Photolysis rate constants of 0.071/hr and 0.033/hr in distilled water were determined for summer and winter conditions, respectively, corresponding to respective half-lives of 10 and 21 hrs(5).

A BCF of 94.7 was experimentally determined for 2,4-dichloroaniline under static conditions in a closed basin with 60 male zebra fish and 5000 ml of carbon filtered tap water(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

The Koc of 2,4-dichloroaniline is 525(1). According to a classification scheme(2), this Koc value suggests that 2,4-dichloroaniline will have low mobility in soil. A Koc of 3930 was measured at pH 6.5 using a colloidal-sized fraction of dissolved organic carbon isolated from groundwater monitoring wells(3). In soil column leaching studies simulating waste leaching from landfill sites, 2,4-dichloroaniline exhibited moderate leaching when leached in combination with leachate from domestic landfill sites(4). Aromatic amines (such as various chloro- and dichloroaniline isomers) have been observed to undergo rapid and reversible covalent bonding with humic materials in aqueous solution. The initial bonding reaction is followed by a slower and much less reversible reaction believed to represent the addition of the amine to quinoidal structures in humic material followed by oxidation of the product to give an amino-substituted quinone(5).

The Henry's Law constant for 2,4-dichloroaniline is estimated as 1.6X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,4-dichloroaniline is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as approximately 711 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as approximately 219 days(SRC). However, the volatilization half-life does not take into account the effects of adsorption. A Koc value of 525(3) suggests that volatilization could be attenuated by adsorption to suspended solids and sediments in water(SRC). This is apparent from the results of two EXAMS model runs, one in which the effect of adsorption was considered, yielding an estimated half-life of 842 days in a model pond 2 m deep, and one in which the effect of adsorption was ignored, yielding an estimated half-life of 317 days in a model pond 2 m deep(4). 2,4-Dichloroaniline's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). 2,4-Dichloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.5X10-2 mm Hg(SRC), determined from a fragment constant method(5).

SURFACE WATER: 2,4-Dichloroaniline was detected at 7 ng/l (minimum) and 26 ng/l (max) upstream of Hamburg, Germany and at 5.3 ng/l (minimum) and 21 ng/l (max) downstream of Hamburg(1). In 1979, 92 surface water samples were collected at 3 sites on the Rhine River and 2 sites on the Meuse River in the Netherlands and Belgium and analyzed for aromatic amines(2). 2,4-Dichloroaniline was detected in 7 of 46 samples at Lobith (Rhine R; 0.76 ppb max, 0.02 ppb mean), 3 of 12 samples at Boven Merwede (Rhine River; 0.15 ppb max, 0.02 ppb mean), 4 of 13 samples at Ijssel (Rhine River; 0.08 ppb max, 0.02 ppb mean), 0 of 9 samples at Eijsden (Meuse River), and 1 of 12 samples at Lith (Meuse Rivers; 0.32 ppb max, 0.03 ppb mean)(2).

2,4-Dichloroaniline was found to occur only once in over 4000 samples of waste waters from 46 industrial categories(1). It was detected in the wastewater effluent generated from the organic chemicals industry, concentration not specified(1). 2,4-Dichloroanilne was detected in sewage sludge from Brandenburg, Germany during the summer at 0.8 mg/kg (median) and 2 mg/kg (max) while during winter it was detected at 0.2 mg/kg (median) and 0.6 mg/kg (max) in sewer sludge dry matter(2).

Occupational exposure to 2,4-dichloroaniline may occur through inhalation and dermal contact with this compound at workplaces where 2,4-dichloroaniline is produced or used(SRC). The general population may be exposed to 2,4-dichloroaniline via ingestion of drinking water(1), dermal contact with this compound in products containing certain dyes, pesticides, and plastics made from 2,4-dichloroaniline(2).

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. 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. /Dichloroanilines; Dichloroanilines, liquid; Dichloroanilines, solid/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Dichloroanilines; Dichloroanilines, liquid; Dichloroanilines, solid/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (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. Ventilate enclosed areas. /Dichloroanilines; Dichloroanilines, liquid; Dichloroanilines, solid/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (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. /Dichloroanilines; Dichloroanilines, liquid; Dichloroanilines, solid/

For more DOT Emergency Guidelines (Complete) data for 2,4-DICHLOROANILINE (8 total), please visit the HSDB record page.

IMO 6.1; Dichloroanilines

UN 1590; Dichloroanilines

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.

Do not transport with food and feedstuffs. Marine pollutant.

Symbol: T, N; R: 23/24/25-33-50/53; S: (1/2)-28-36/37-45-60-61; Note: C

UN Hazard Class: 6.1; UN Pack Group: II