2-Chloroaniline

Nitrogen Compounds -> Amines, Aromatic

Textile

log Kow = 1.90

1.92

1.74

Characteristic sweet odor

Amine odor

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

1.2114 at 22 °C/4 °C

1.213 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.00

Amber liquid

Water-white to tan liquid

Colorless liquid

less than 1 mg/mL at 68 °F (NTP, 1992)

Soluble in acid and in most organic solvents.

Miscible in alcohol and ether

Soluble in alcohol, ether, benzene, and acetone.

In water, 8165 mg/L at 25 °C

Solubility in water, g/100ml at 20 °C: 0.5

208 °F (NTP, 1992)

103 °C

103 °C (closed cup)

108 °C

406 to 410 °F at 760 mmHg (NTP, 1992)

208.8 °C

209 °C

28.5 °F (NTP, 1992)

-14 °C

-2 °C

Danger

H301+H311+H331 (78.9%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

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

Aggregated GHS information provided per 204 reports by companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

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

Chemical: Benzenamine, 2-chloro-

Benzenamine, 2-chloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, 2-chloro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 15-04-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13785

2-Chloroaniline: Does not have an individual approval but may be used under an appropriate group standard

This chemical is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

SYMPTOMS: Symptoms of exposure to this compound may include headache, nausea, vomiting, jaundice, convulsions, severe kidney damage, liver damage, methemoglobin formation and in sufficient concentrations, cyanosis; skin and eye irritation; and dermatitis. Onset may be delayed 2-4 hours or longer.

o-Chloroaniline is listed in a table Examples of Industrial Chemicals for Which Methemoglobin Formation is the Principal Cause of Toxicity; [ACGIH] 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. (Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988.) An eye irritant; Can induce methemoglobinemia; [ICSC] Negative results for skin sensitizer from guinea pig testing; [Reference #2]

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Benzenamine, 2-chloro- is included on this list.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. o-chloroaniline is produced, as an intermediate or a final product, by process units covered under this subpart.

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

Use powder. Use foam. Use carbon dioxide.

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.

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed 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.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

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 in an incinerator.

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.

EC50 Daphnia magna (Daphnids; ability to swim) 4.2 mg/L/24 hr /Conditions of bioassay not specified in source examined/

EC50 Daphnia magna (Daphnids; ability to swim) 1.8 mg/L/48 hr /Conditions of bioassay not specified in source examined/

LC50 Tubifex (Worm) 130-220 mg/L/48 hr

LC50 Oryzia latipes (Medaka) 6.4 mg/L/48 hr /Conditions of bioassay not specified in source examined/

For more Ecotoxicity Values (Complete) data for 2-CHLOROANILINE (9 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 260(SRC), determined from a log Kow of 1.90(2) and a regression-derived equation(3), indicates that 2-chloroaniline is expected to have moderate mobility in soil(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(4,5), suggesting that mobility may be much lower in some soils(SRC). The pKa of 2-chloroaniline is 2.66(6), indicating that this compound will primarily exist in its nonionic form in the environment. Volatilization of 2-chloroaniline from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.4X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.20 mm Hg(7), and water solubility, 8.2X10+3 mg/L(8). However, adsorption to soil is expected to attenuate volatilization(SRC). 2-Chloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.20 mm Hg(7). Biodegradation screening tests suggest that 2-chloroaniline is slightly to non-biodegradable(9,10). 100% loss of UV absorbance by microbial degradation in a mineral salts solution, with a soil inoculum, required an excess of 64 days(11). When 2-chloroaniline (3-ppm) was incubated in Guelph loam with water added to 60% water-holding capacity, levels declined rapidly for 2 weeks after which time the rate of loss decreased(12). The percent of 2-chloroaniline remaining in soil after 2 and 8 weeks were 40 and 20%, respectively(12). Experiments using 2-chloroaniline show that it undergoes photolysis in aqueous solution when irradiated by light with wavelengths above 290 nm (13,14); 2-chloroaniline may also be susceptible to direct photolysis by sunlight in soil surfaces(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 260(SRC), determined from a log Kow of 1.90(2) and a regression-derived equation(3), indicates that 2-chloroaniline is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 5.4X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.20 mm Hg(4), and water solubility, 8.2X10+3 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 7.8 days and 60 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 group(6,7), 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 2-chloroaniline is 2.66(8), indicating that this compound will primarily exist in its nonionic form in the environment. According to a classification scheme(9), an estimated BCF of 5.8(SRC), from an estimated log Kow(2) and a regression-derived equation(10), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation screening tests suggest that 2-chloroaniline is generally resistant to biodegradation or biodegrades slowly(11,12). 2-Chloroaniline (2 mg/L) was found to be not readily biodegradable with a 10% BOD observed after 5 days in a mixed inoculum of river water collected from the Songhua River in China(13). Irradiation of an aqueous solution of 2-chloroaniline in a quartz tube with a fluorochemical lamp (wavelengths above 300 nm) resulted in a photodegradation half-life of 11.5 hours(14). When aqueous solutions of 2.5X10-3 mol/L 2-chloroaniline in a photochemical reactor were irradiated by a mercury lamp (wavelengths 254, 297, and 365 nm), the concentration of 2-chloroaniline decreased exponentially with time, and the rate of disappearance approximated a first-order process with a rate constant of 0.107/hour(15).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-chloroaniline, which has a vapor pressure of 0.20 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-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 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(3). 2-Chloroaniline absorbs ultraviolet light above 290 nm(4). Experiments using 2-chloroaniline show that it undergoes photolysis in aqueous solution when irradiated by light with wavelengths above 290 nm (5,6); 2-chloroaniline may also be susceptible to direct photolysis by sunlight in air(SRC).

/AQUATIC SPECIES/ 21 day Daphnia reproduction tests were conducted in line with the provisional procedure proposed by the Federal Environmental Agency (Umweltbundesamt, FRG), as of Jan 1, 1984. Groups of 20, 24-hr old Daphnia magna Straus were exposed to 0.001 to 3.16 mg/L 2-chloroaniline in semi-static test vessels. Parent animals in the test and control vessels had to be pipetted 3 times/wk in freshly prepared test and control media at the corresponding concentration level. The no observed effect concentration (NOEC) was determined from the parameters of mortality of the parent animals, reproduction rate and appearance of the first offspring during the test period. In preliminary acute Daphnia tests, the 24-hr EC50 was 6.0 mg/L for 2-chloroaniline, the EC0 was 1.4 mg/L. The nominal 21-day no observed effect concentration was 0.032 mg/L.

/AQUATIC SPECIES/ Twenty-nine day old fathead minnows were exposed to an 80 mg/L concentration of 2-chloroaniline. Test conditions were as follows: Exposure temperature: 24.9 °C; pH: 7.60. Average concentration/chamber of 2-chloroaniline ranged from 2.00-25.9 mg/L. Affected fathead minnows lost schooling behavior and swam near the tank surface. They were hyperactive and overreactive to external stimuli, were darkly colored, and hemorrhagic. Equilibrium loss was not observed prior to death.

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

MAY BE ABSORBED! Further see Inhalation.

Redness. Pain.

Abdominal pain. Further see Inhalation.

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. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=95-51-2]

2-Chloroaniline was detected at an average concentration of 42.58 ug/L and a 76.5% frequency of detection in sewage treatment effluents in England and Wales collected in 1995(1). In a comprehensive survey of wastewater from 4,000 industrial and publicly owned treatment works sponsored by the Effluent Guidelines Division of the US EPA, 2-chloroaniline was identified in discharges of the following industrial categories (positive occurrences, median concentration in ppb): pharmaceuticals (4; 588.1) and organic chemicals (3; 57.1)(2). The highest effluent concentration was 2564.1 ppb in the pharmaceutical industry(2). Wastewater discharges from the commercial manufacture of 4,4'-methylenebis(2-chloroaniline) can contain 2-chloroaniline(3). 2-Chloroaniline was qualitatively detected in effluent discharges from chemical production facilities along the Upper Catawba River in North Carolina in 1973 and 1974(4). Sludge from the Muskegon County, Michigan wastewater treatment system was found to contain 48.3 mg/kg 2-chloroaniline(5).

The Koc of 2-chloroaniline is estimated as 260(SRC), using a log Kow of 1.9(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2-chloroaniline is expected to have moderate mobility in soil. 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 much lower in some soils(SRC).

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Benzenamine, 2-chloro- is included on this list.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. o-chloroaniline is produced, as an intermediate or a final product, by process units covered under this subpart.

o-Chloroaniline in rabbits is metabolized to 2-amino-3-chlorophenol and 4-amino-3-chlorophenol. In soya beans it yields o-chloroaniline-n-glucoside. /from table/

Bacillus firmus was isolated and transformed 2-chloroaniline almost quantitatively into 4-chloroacetanilide with smaller amount of 4-chloropropionanilide according to co-metabolic reaction.

The primary metabolite of either 2-chloroaniline or 4-chloroaniline by a faecalis in a liquid culture was 4-chloropyrocatechin, further metabolized to 5-chloro-2-hydroxymuconic acid semialdehyde, which was in turn metabolized with the NAD+ cosubstrate to 2-chloro-4-oxalocrotonic acid.

Studies in rats and rabbits have shown that like other aromatic amines, the compound is oxidized in microsomes of liver, kidney, and lung by cytochrome P450 oxidases to its hydroxylated derivatives, which undergo N-acetylation and/or conjugation with glucuronic and sulfuric acids, with subsequent excretion in the urine and/or dissociation into reactive metabolites in the bladder of some species such as the dog and the human.

For more Metabolism/Metabolites (Complete) data for 2-CHLOROANILINE (7 total), please visit the HSDB record page.

The compound is absorbed through the intact skin. o-Chloroaniline is absorbed by oral, inhalation, or dermal exposure.

... Male Fischer 344 rats (4/group) were administered [14C]-2-chloroaniline or [14C]-4-chloroaniline (0.5 or 1.0 mmol/kg; approximately 50 uCi/rat) ip. Urine, feces, blood and tissues were collected at 3 and 24 hr. Both 2- and 4-chloroaniline-derived radioactivity were primarily renally excreted with <1% excretion in the feces by 24 hr post-treatment. Both chloroanilines accumulated mainly in liver (percentage of administered dose/total tissue), but kidney generally had similar or higher equivalent concentrations (umol/g tissue) compared to liver. Subcellular distribution revealed that for both chloroanilines, the cytosolic fraction generally had the highest level of radioactivity independent of time or dose. Covalent binding was detected in both liver and kidney, with the highest concentration (pmol/mg protein) of binding observed in the hepatic microsomal fraction regardless of compound, dose or time studied. In general, 2-chloroaniline derived radioactivity was excreted faster, reached peak tissue concentrations earlier, disappeared from tissues faster and had less covalent binding in target tissue at 24 hr than 4-chloroaniline-derived radioactivity.

Used as an intermediate for dyes, pesticides, and rubber chemicals; [HSDB]

... Intermediate for rubber chemicals, pigments, pesticides and dyes.

Dye intermediate, standards for colorimetric apparatus, manufacture of petroleum solvents and fungicides.

GRADES:Technical

Liquid, technical grades

Synthetic Rubber Manufacturing

Benzenamine, 2-chloro-: ACTIVE