4-Bromoaniline

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

H311 (94.3%): Toxic in contact with skin [Danger Acute toxicity, dermal]

H315 (90.6%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (90.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H332 (17%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H335 (75.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

H373 (20.8%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

P260, P261, P262, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 53 reports by companies from 12 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.

Fresh air, rest. Refer for medical attention.

Rinse and then wash skin with water and soap.

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)

Fires involving this compound should be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray, powder, foam, carbon dioxide.

Special protective equipment for firefighters Wear self contained breathing apparatus for fire fighting if necessary.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-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)

Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment.

Removal of chloroaniline from wastewater by electrochemical treatment is discussed. /4-Chloroaniline/

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 after burner and scrubber. /4-Chloroaniline/

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

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. /4-Chloroaniline/

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. Ensure that the local ventilation moves the contaminant away from the worker.

Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.

Do not eat, drink, or smoke during work.

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 in a freezer. (NTP, 1992)

Separated from strong oxidants and acids. Well closed.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection. Conditions for safe storage Keep container tightly closed in a dry and well-ventilated place. Light sensitive. Store under inert gas. Air sensitive.

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 may cause effects on the blood. This may result in the formation of methaemoglobin. 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)

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

Protective gloves.

Use local exhaust or breathing protection.

Skin and body protection: Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

For more Personal Protective Equipment (PPE) (Complete) data for 4-BROMOANILINE (7 total), please visit the HSDB record page.

NO open flames.

STRICT HYGIENE!

Do not eat, drink, or smoke during work.

P-bromoaniline is a brown solid with a sweet odor. (NTP, 1992)

Colorless solid; [Hawley] Brown solid; [CAMEO] White or brown powder; [MSDSonline]

COLOURLESS CRYSTALS.

Bipyramidal rhombic crystals, needles from 60% alcohol

Colorless crystals

Decomposes (NTP, 1992)

219.7 °C

BP: decomposes

151.5 °F (NTP, 1992)

66-66.5 °C

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

Very soluble in alcohol and ether; insoluble in cold water

Solubility in water: poor

1.497 at 212 °F (NTP, 1992) - Denser than water; will sink

1.4970 at 99.6 °C/4 °C

Relative density (water = 1): 1.5 (100 °C)

5.9 (Air = 1)

Relative vapor density (air = 1): 5.9

0.04 [mmHg]

Vapor pressure, Pa at 25 °C: 22.6

log Kow = 2.26

pKa = 3.86 at 25 °C (conjugate acid)

Dissociation constant pKb = 10.28 at 25 °C (also reported as 9.98)

Aqueous solutions of 4-bromoaniline are slightly alkaline

UV: 6-68 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York) /3-Bromoaniline/

13C nuclear magnetic resonance spectrum

15N nuclear magnetic resonance spectrum

Chemical shift

Diamagnetic susceptibility

Magnetic susceptibility

Nuclear quadrupole resonance spectroscopy

Quadrupole coupling

Spin-spin coupling constant

Viscosity

Nitrogen Compounds -> Amines, Aromatic

Environmental transformation -> Pesticide transformation products (metabolite, successor)

This material is sensitive to prolonged exposure to air. Vapor may form highly reactive mixtures in air (NTP, 1992). Insoluble in water.

Aryl Halides

Amines, Aromatic

Vapor may form highly reactive mixtures in air. (NTP, 1992)

The solution in water is a weak base. Reacts with acids and strong oxidants.

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.

Blue lips, fingernails and skin. Headache. Nausea.

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

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

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aniline and related compounds/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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 0.9% saline (NS) 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/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive with a normal fluid volume. 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. ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aniline and related compounds/

/LABORATORY ANIMALS: Neurotoxicity/ The potential for neurotoxicity after a single oral dose of four halogenated aniline derivatives--4-bromoaniline, 4-chloroaniline, 4- fluoroaniline and 4-iodoaniline --was given to rats was investigated at or near the lethal dosage level /500 mg/kg 4-bromoaniline, 300 mg/kg 4-chloroaniline, 600 mg/kg 4-fluoroaniline, 700 mg/kg 4-iodoaniline/. Hindlimb paralysis was found in the 4-bromoaniline, 4-chloroaniline and 4- fluoroaniline groups on clinical observation, with the maximum incidence of 100% in the 4-bromoaniline and 4- fluoroaniline groups and 66.7% in the 4-chloroaniline group. Detailed clinical observations with functional tests identified the following effects: reduced response of hindlimb extensor thrust, gait abnormality in the open field and decreased grip strength in the fore- or hindlimbs in the 4-bromoaniline, 4-chloroaniline and 4- fluoroaniline groups; decreased number of supported rearing episodes in the open field in the 4-bromoaniline and 4-chloroaniline groups; abnormal landing in the aerial righting reflex in the 4-bromoaniline and 4- fluoroaniline groups; and prolonged surface righting reflex in the 4-bromoaniline group. Spongy change in the white matter of the spinal cord and brainstem and nerve fibre degeneration in the peripheral nerves were found in all haloaniline-treated groups. The central and peripheral nervous systems were most severely affected in the 4-bromoaniline group and the lesions in the 4-IA group were limited in grade. This study demonstrates that a bolus dose of 4-haloanilines to rats induces a neurotoxicity similar in character to that evoked by the parent aniline. The decreasing order of neurotoxic potential appears to be 4-bromoaniline >> 4- fluoroaniline > or = 4-chloroaniline >> 4-iodoaniline when comparing at or near the lethal dosage level.

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from, as of July 17, 2013: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=106-40-1]

LC50; Species: Pimephales promelas (Fathead Minnow) age 26-34 day juvenile; Conditions: freshwater, flow through, 25 °C, pH 7.8, hardness 45 mg/L CaCO3, alkalinity 42 mg/L CaCO3; Concentration: 47500 ug/L for 96 hr /> or =95% purity/

The substance is harmful to aquatic organisms.

4-Bromoaniline's production and use as an intermediate in the production of azo dyes, dihydroquinazolines, metobromuron and resorantel may result in its release to the environment through various waste streams. It can also be released to the environment as a product of the microbial breakdown of the herbicide metobromuron in soil. If released to air, an estimated vapor pressure of 0.05 mm Hg at 25 °C indicates 4-bromoaniline will exist primarily as a vapor in the atmosphere. However, 4-bromoaniline has been detected in atmospheric particulate matter. Vapor-phase 4-bromoaniline 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 12 hours. Particulate-phase 4-bromoaniline will be removed from the atmosphere by wet and dry deposition. 4-Bromoaniline absorbs at wavelengths >290 nm and, therefore, may be susceptible to direct photolysis by sunlight. If released to soil, 4-bromoaniline is expected to have high to moderate mobility based upon measured Koc values of 91 and 218. However, anilines 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. Photodegradation may be possible on soil surfaces exposed to sunlight. 4-Bromoaniline has been shown to be biodegradable in acclimated soil and water, but biodegradation may be very slow in unacclimated soil. Volatilization from moist soil surfaces may have some importance based upon an estimated Henry's Law constant of 9.1X10-7 atm-cu m/mole. If released into water, 4-bromoaniline is not expected to adsorb to suspended solids and sediment based upon the Koc values. However, some binding to suspended organic matter and sediment may occur due to the high reactivity of the aromatic amino group. Biodegradation of 4-bromoaniline has been observed in Elbe River water and anaerobic estuarine sediment. 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 53 and 389 days, respectively. An estimated BCF of 14 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 (pH 5 to 9). Both direct and indirect photolysis may have some importance in natural waters exposed to sunlight. Occupational exposure to 4-bromoaniline may occur through inhalation of aerosols and dermal contact with this compound at workplaces where 4-bromoaniline is produced or used. Monitoring data indicate that the general population may be exposed to 4-bromoaniline via inhalation of ambient air. (SRC)

4-Bromoaniline's production and use as an intermediate in the production of azo dyes, dihydroquinazolines, metobromuron and resorantel(1,2) may result in its release to the environment through various waste streams(SRC). 4-Bromoaniline was qualitatively detected in stack effluents generated by hazardous waste incineration(3). It may also be released to the environment as a product of the microbial breakdown of the herbicide metobromuron in soil(4). 4-Bromoaniline has been detected in tobacco grown in soil treated with metobromuron(5).

TERRESTRIAL FATE: Based on a classification scheme(1), measured Koc values of 91(2) and 218(3) indicate that 4-bromoaniline is expected to have high to moderate mobility in soil(SRC). The pKa of 4-bromoaniline is 3.86(4), indicating that this compound is a weak base and will exist predominantly in the non-ionized form in the environment. However, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(5,6), suggesting that mobility may be much lower in some soils(SRC). 4-Bromoaniline absorbs at wavelengths >290 nm(7) and, therefore, may be susceptible to direct photolysis on soil surfaces exposed to sunlight(SRC). 4-Bromoaniline has been shown to be biodegradable in acclimated soil and water(8,9), but biodegradation may be very slow in unacclimated soil(8). Volatilization of 4-bromoaniline from moist soil surfaces may have some importance(SRC) given an estimated Henry's Law constant of 9.1X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(10).

AQUATIC FATE: Based on a classification scheme(1), measured Koc values of 91(2) and 218(3) indicate that 4-bromoaniline is not expected to adsorb to suspended solids and sediment(SRC). The pKa of 4-bromoaniline is 3.86(4), indicating that this compound is a weak base and will exist predominantly in the non-ionized form in the environment. Anilines may bind strongly to humus or organic matter due to the high reactivity of the aromatic amino group(5,6), suggesting some adsorption to suspended solids and sediment may occur(SRC). Volatilization from water surfaces is expected(7) based upon an estimated Henry's Law constant of 9.1X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(8). Using this Henry's Law constant and an estimation method(7), volatilization half-lives for a model river and model lake are 53 and 389 days, respectively(SRC). According to a classification scheme(9), an estimated BCF of 14(SRC), from its log Kow of 2.26(10) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 4-Bromoaniline absorbs at wavelengths >290 nm(11) and, therefore, may be susceptible to direct photolysis(SRC). Aromatic amines are susceptible to photosensitized degradation in natural waters exposed to sunlight due to reaction with OH and RO2 radicals(12); therefore, indirect photolysis may have some environmental importance in natural water(SRC). 4-Bromoaniline is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(7). In biodegradation studies using Elbe River water and a testfilter methodology, 4-bromoaniline had a mean degradation rate of 0.67/hr (half-life of about 1 hour; half-life in control samples was 99 hrs)(13). In anaerobic biodegradation tests using an estuarine sediment from the Tsurumi River in Japan, 4-bromoaniline had an observed degradation rate of 0.00557/day which corresponded to a half-life of 124.4 days(14).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-bromoaniline, which has an estimated vapor pressure of 0.05 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist primarily as a vapor in the ambient atmosphere. However, monitoring data have detected 4-bromoaniline in ambient atmospheric particulate material at relatively high concentrations of 109 ng/cu m(3). Vapor-phase 4-bromoaniline 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 12 hours(SRC), calculated from its rate constant of 3.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase 4-bromoaniline may be removed from the air by wet and dry deposition(SRC). 4-Bromoaniline absorbs at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

AEROBIC: Soil enrichment cultures extracted from soils that had been treated with herbicides (such as linuron and metobromuron) over multiple years were able to readily degrade the herbicides and their degradation products (4-bromoaniline was the degradation product from metobromuron)(1); untreated control soil samples from the same location did not show any degradation activity(1). In biodegradation studies using Elbe River water and a testfilter methodology, 4-bromoaniline had a mean degradation rate of 0.67/hr (half-life of about 1 hour)(2); degradation rate in control samples was only 0.007/hr (half-life of 99 hours)(2).

ANAEROBIC: In anaerobic biodegradation tests using an estuarine sediment from the Tsurumi River in Japan, 4-bromoaniline had an observed degradation rate of 0.00557/day which corresponded to a half-life of 124.4 days(1).

PURE CULTURE: Purified enzymes of the soil fungus Geotrichum candidum biotransformed p-bromoaniline to 4,4'- dibromoazobenzene(1). A strain of Moraxella sp used p-bromoaniline as a sole source of carbon and nitrogen(2).

The rate constant for the vapor-phase reaction of 4-bromoaniline with photochemically-produced hydroxyl radicals has been estimated as 3.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 12 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 4-Bromoaniline absorbs at wavelengths >290 nm(2,3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Aromatic amines are susceptible to photosensitized degradation in natural waters exposed to sunlight due to reaction with OH and RO2 radicals(4); therefore, indirect photolysis may have some environmental importance in natural water(SRC). 4-Bromoaniline is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(5).

An estimated BCF of 14 was calculated in fish for 4-bromoaniline(SRC), using a log Kow of 2.26(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Soil adsorption studies using four silt loam soils and a 2-hour adsorption period determined a mean log Kom (K organic matter) of 1.72 (which corresponds to a log Koc of 1.96 and Koc of 91 for 4-bromoaniline(1). A Koc of 217.9 was determined in sorption studies using a calcareous Spanish soil(2); manual addition of dissolved organic carbon (from peat or tannic acid) was found to increase 4-bromoanline adsorption on soil(2). According to a classification scheme(3), these Koc values suggests that 4-bromoaniline is expected to have moderate to high mobility in soil. The pKa of 4-bromoaniline is 3.86(4), indicating that this compound is a weak base and will exist predominantly in the non-ionized form in the environment. However, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(5,6), suggesting that mobility may be much lower in some soils(SRC).

The Henry's Law constant for 4-bromoaniline is estimated as 9.1X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 4-bromoaniline 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 53 days(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 389 days(SRC). 4-Bromoaniline's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 4-Bromoaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.05 mm Hg at 25 °C(SRC), determined from a fragment constant method(1).

SURFACE WATER: p-Bromoaniline was qualitatively detected in surface waters from agricultural areas draining into Rhine delta waters; year and exact sampling locations not specified(1).

4-Bromoaniline was qualitatively detected in stack effluents generated by hazardous waste incineration(1).

URBAN/SUBURBAN: Atmospheric particulate samples collected in the city of Lanzhou China in March 2003 contained 4-bromoaniline concentration of 109 ng/cu m(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 4,702 workers (3,745 of these were female) were potentially exposed to 4-bromoaniline in the US(1). Occupational exposure to 4-bromoaniline may occur through inhalation of aerosols(2) and dermal contact with this compound at workplaces where 4-bromoaniline is produced or used(SRC). Monitoring data indicate that the general population may be exposed to 4-bromoaniline via inhalation of ambient air(SRC).

LC50; Species: Pimephales promelas (Fathead Minnow) age 26-34 day juvenile; Conditions: freshwater, flow through, 25 °C, pH 7.8, hardness 45 mg/L CaCO3, alkalinity 42 mg/L CaCO3; Concentration: 47500 ug/L for 96 hr /> or =95% purity/

The substance is harmful to aquatic organisms.

4-Bromoaniline's production and use as an intermediate in the production of azo dyes, dihydroquinazolines, metobromuron and resorantel may result in its release to the environment through various waste streams. It can also be released to the environment as a product of the microbial breakdown of the herbicide metobromuron in soil. If released to air, an estimated vapor pressure of 0.05 mm Hg at 25 °C indicates 4-bromoaniline will exist primarily as a vapor in the atmosphere. However, 4-bromoaniline has been detected in atmospheric particulate matter. Vapor-phase 4-bromoaniline 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 12 hours. Particulate-phase 4-bromoaniline will be removed from the atmosphere by wet and dry deposition. 4-Bromoaniline absorbs at wavelengths >290 nm and, therefore, may be susceptible to direct photolysis by sunlight. If released to soil, 4-bromoaniline is expected to have high to moderate mobility based upon measured Koc values of 91 and 218. However, anilines 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. Photodegradation may be possible on soil surfaces exposed to sunlight. 4-Bromoaniline has been shown to be biodegradable in acclimated soil and water, but biodegradation may be very slow in unacclimated soil. Volatilization from moist soil surfaces may have some importance based upon an estimated Henry's Law constant of 9.1X10-7 atm-cu m/mole. If released into water, 4-bromoaniline is not expected to adsorb to suspended solids and sediment based upon the Koc values. However, some binding to suspended organic matter and sediment may occur due to the high reactivity of the aromatic amino group. Biodegradation of 4-bromoaniline has been observed in Elbe River water and anaerobic estuarine sediment. 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 53 and 389 days, respectively. An estimated BCF of 14 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 (pH 5 to 9). Both direct and indirect photolysis may have some importance in natural waters exposed to sunlight. Occupational exposure to 4-bromoaniline may occur through inhalation of aerosols and dermal contact with this compound at workplaces where 4-bromoaniline is produced or used. Monitoring data indicate that the general population may be exposed to 4-bromoaniline via inhalation of ambient air. (SRC)

4-Bromoaniline's production and use as an intermediate in the production of azo dyes, dihydroquinazolines, metobromuron and resorantel(1,2) may result in its release to the environment through various waste streams(SRC). 4-Bromoaniline was qualitatively detected in stack effluents generated by hazardous waste incineration(3). It may also be released to the environment as a product of the microbial breakdown of the herbicide metobromuron in soil(4). 4-Bromoaniline has been detected in tobacco grown in soil treated with metobromuron(5).

TERRESTRIAL FATE: Based on a classification scheme(1), measured Koc values of 91(2) and 218(3) indicate that 4-bromoaniline is expected to have high to moderate mobility in soil(SRC). The pKa of 4-bromoaniline is 3.86(4), indicating that this compound is a weak base and will exist predominantly in the non-ionized form in the environment. However, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(5,6), suggesting that mobility may be much lower in some soils(SRC). 4-Bromoaniline absorbs at wavelengths >290 nm(7) and, therefore, may be susceptible to direct photolysis on soil surfaces exposed to sunlight(SRC). 4-Bromoaniline has been shown to be biodegradable in acclimated soil and water(8,9), but biodegradation may be very slow in unacclimated soil(8). Volatilization of 4-bromoaniline from moist soil surfaces may have some importance(SRC) given an estimated Henry's Law constant of 9.1X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(10).

AQUATIC FATE: Based on a classification scheme(1), measured Koc values of 91(2) and 218(3) indicate that 4-bromoaniline is not expected to adsorb to suspended solids and sediment(SRC). The pKa of 4-bromoaniline is 3.86(4), indicating that this compound is a weak base and will exist predominantly in the non-ionized form in the environment. Anilines may bind strongly to humus or organic matter due to the high reactivity of the aromatic amino group(5,6), suggesting some adsorption to suspended solids and sediment may occur(SRC). Volatilization from water surfaces is expected(7) based upon an estimated Henry's Law constant of 9.1X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(8). Using this Henry's Law constant and an estimation method(7), volatilization half-lives for a model river and model lake are 53 and 389 days, respectively(SRC). According to a classification scheme(9), an estimated BCF of 14(SRC), from its log Kow of 2.26(10) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 4-Bromoaniline absorbs at wavelengths >290 nm(11) and, therefore, may be susceptible to direct photolysis(SRC). Aromatic amines are susceptible to photosensitized degradation in natural waters exposed to sunlight due to reaction with OH and RO2 radicals(12); therefore, indirect photolysis may have some environmental importance in natural water(SRC). 4-Bromoaniline is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(7). In biodegradation studies using Elbe River water and a testfilter methodology, 4-bromoaniline had a mean degradation rate of 0.67/hr (half-life of about 1 hour; half-life in control samples was 99 hrs)(13). In anaerobic biodegradation tests using an estuarine sediment from the Tsurumi River in Japan, 4-bromoaniline had an observed degradation rate of 0.00557/day which corresponded to a half-life of 124.4 days(14).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-bromoaniline, which has an estimated vapor pressure of 0.05 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist primarily as a vapor in the ambient atmosphere. However, monitoring data have detected 4-bromoaniline in ambient atmospheric particulate material at relatively high concentrations of 109 ng/cu m(3). Vapor-phase 4-bromoaniline 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 12 hours(SRC), calculated from its rate constant of 3.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase 4-bromoaniline may be removed from the air by wet and dry deposition(SRC). 4-Bromoaniline absorbs at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

AEROBIC: Soil enrichment cultures extracted from soils that had been treated with herbicides (such as linuron and metobromuron) over multiple years were able to readily degrade the herbicides and their degradation products (4-bromoaniline was the degradation product from metobromuron)(1); untreated control soil samples from the same location did not show any degradation activity(1). In biodegradation studies using Elbe River water and a testfilter methodology, 4-bromoaniline had a mean degradation rate of 0.67/hr (half-life of about 1 hour)(2); degradation rate in control samples was only 0.007/hr (half-life of 99 hours)(2).

ANAEROBIC: In anaerobic biodegradation tests using an estuarine sediment from the Tsurumi River in Japan, 4-bromoaniline had an observed degradation rate of 0.00557/day which corresponded to a half-life of 124.4 days(1).

PURE CULTURE: Purified enzymes of the soil fungus Geotrichum candidum biotransformed p-bromoaniline to 4,4'- dibromoazobenzene(1). A strain of Moraxella sp used p-bromoaniline as a sole source of carbon and nitrogen(2).

The rate constant for the vapor-phase reaction of 4-bromoaniline with photochemically-produced hydroxyl radicals has been estimated as 3.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 12 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 4-Bromoaniline absorbs at wavelengths >290 nm(2,3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Aromatic amines are susceptible to photosensitized degradation in natural waters exposed to sunlight due to reaction with OH and RO2 radicals(4); therefore, indirect photolysis may have some environmental importance in natural water(SRC). 4-Bromoaniline is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(5).

An estimated BCF of 14 was calculated in fish for 4-bromoaniline(SRC), using a log Kow of 2.26(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Soil adsorption studies using four silt loam soils and a 2-hour adsorption period determined a mean log Kom (K organic matter) of 1.72 (which corresponds to a log Koc of 1.96 and Koc of 91 for 4-bromoaniline(1). A Koc of 217.9 was determined in sorption studies using a calcareous Spanish soil(2); manual addition of dissolved organic carbon (from peat or tannic acid) was found to increase 4-bromoanline adsorption on soil(2). According to a classification scheme(3), these Koc values suggests that 4-bromoaniline is expected to have moderate to high mobility in soil. The pKa of 4-bromoaniline is 3.86(4), indicating that this compound is a weak base and will exist predominantly in the non-ionized form in the environment. However, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(5,6), suggesting that mobility may be much lower in some soils(SRC).

The Henry's Law constant for 4-bromoaniline is estimated as 9.1X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 4-bromoaniline 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 53 days(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 389 days(SRC). 4-Bromoaniline's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 4-Bromoaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.05 mm Hg at 25 °C(SRC), determined from a fragment constant method(1).

SURFACE WATER: p-Bromoaniline was qualitatively detected in surface waters from agricultural areas draining into Rhine delta waters; year and exact sampling locations not specified(1).

4-Bromoaniline was qualitatively detected in stack effluents generated by hazardous waste incineration(1).

URBAN/SUBURBAN: Atmospheric particulate samples collected in the city of Lanzhou China in March 2003 contained 4-bromoaniline concentration of 109 ng/cu m(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 4,702 workers (3,745 of these were female) were potentially exposed to 4-bromoaniline in the US(1). Occupational exposure to 4-bromoaniline may occur through inhalation of aerosols(2) and dermal contact with this compound at workplaces where 4-bromoaniline is produced or used(SRC). Monitoring data indicate that the general population may be exposed to 4-bromoaniline via inhalation of ambient air(SRC).

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

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. /4-Chloroaniline/