3-Chloranilin

log Kow = 1.88

1.9

1.9

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

1.2150 at 22 °C/4 °C

Relative density (water = 1): 1.216

less than 1 mg/mL at 64 °F (NTP, 1992)

Soluble in most common organic solvents

Miscible in ethanol, ether, and acetone

In water, 5,400 mg/L at 20 °C

Solubility in water, g/100ml at 20 °C: 0.6

255 °F (NTP, 1992)

255 °F

118 °C c.c.

446.9 °F at 760 mmHg (NTP, 1992)

230.5 °C

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

230 °C

13.5 °F (NTP, 1992)

-10.4 °C

-10 °C

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

Relative vapor density (air = 1): 4.4

Danger

H301+H311 (25%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]

P203, P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P320, P321, P330, P333+P317, P337+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 160 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

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

Chemical: Benzenamine, 3-chloro-

Commission Regulation No 844/2012

Benzenamine, 3-chloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, 3-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: Cease Manufacture Update: 07-11-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/6855

3-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.

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.) A skin and eye irritant; Can induce methemoglobinemia; [ICSC] Danger of skin sensitization; [MAK]

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, 3-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. m-chloroaniline is produced, as an intermediate or a final product, by process units covered under this subpart.

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

Use powder, AFFF, foam, 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 of in an incinerator.

...Precaution should be taken to avoid inhalation of vapors.

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.

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

LC50 Eisenia andrei (Earthworm) 568-725 ug/L/14 days

LC50 Lumbricus rubellus (Earthworm) 388-469 ug/L/14 days

LC50 Poecilia reticulata (Guppy) 13 mg/L/14 days /Conditions of bioassay not specified in source examined/

LC50 Crangon septemspinosa (Bay shrimp, Sand shrimp) 25 mg/L/96 hr; renewal, aerated sea water, 10 °C

For more Ecotoxicity Values (Complete) data for 3-CHLOROANILINE (9 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 250(SRC), determined from a log Kow of 1.88(2) and a regression-derived equation(3), indicates that 3-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). 3-Chloroaniline may undergo covalent chemical bonding with humic materials which results in its chemical alteration and tight adsorption(6). There is evidence to suggest that this complexing may extend the residual life of these substances in soil for as much as 10 years(7). Due to this covalent bonding, significant leaching in soil systems is not generally expected to occur(SRC). The pKa of 3-chloroaniline is 3.52(10), indicating that this compound will primarily exist in its nonionic form in the environment. Volatilization of 3-chloroaniline from moist soil surfaces is expected to occur(SRC) given a Henry's Law constant of 1.0X10-6 atm-cu m/mole(8). However, adsorption to soil is expected to attenuate volatilization(SRC). 3-Chloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.066 mm Hg(9). 3-Chloroaniline may degrade in soil by chemical and microbial processes(11). When 3-chloroaniline (30 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(11). The percent of 3-chlororaniline remaining in soil after 2 and 8 weeks were 38% and 18%, respectively(11).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 250(SRC), determined from a log Kow of 1.88(2) and a regression-derived equation(3), indicates that 3-chloroaniline may adsorb to suspended solids and sediment(SRC). In addition, 3-chloroaniline may undergo chemical bonding with humic materials in the water column and in the sediment(4). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.0X10-6 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 42 and 310 days, respectively(SRC). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(13,14), 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 3-chloroaniline is 3.52(6), indicating that this compound will primarily exist in its nonionic form in the environment. According to a classification scheme(7), measured BCF values ranging from 0.8 to 11.5(8,9) suggests the potential for bioconcentration in aquatic organisms is low(SRC). In a 3-day cultivation test using 2 different river waters from Japan and two different sea waters, 50% of initial 3-chloroaniline was degraded; the degradation was paralleled by growth of microbes(9,10). A biotransformation half-life of 0.4 year was determined for 3-chloroaniline in laboratory studies using two pond and one river water samples obtained near Athens, GA(12). Irradiation of an aqueous solution of 3-chloroaniline in a quartz tube with a fluorochemical lamp (wavelengths above 300 nm) resulted in a photodegradation half-life of 2.6 hours(14).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-chloroaniline, which has a vapor pressure of 0.066 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 3-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 5.1 hours(SRC), calculated from its rate constant of 7.6X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 3-Chloroaniline absorbs light with wavelengths >290 nm(4) and may be susceptible to direct photolysis by sunlight(SRC).

/AQUATIC SPECIES/ 21 day Daphnia reproduction tests were conducted in line with the provisional procedure proposed by the Federal Environmental Agency, as of Jan 1, 1984. Groups of 20, 24-hr old Daphnia magna Straus were exposed to 6.3 to 800 ug/L 3-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 0.9 mg/L for 3-chloroaniline, the EC0 was 0.40 mg/L. The nominal 21 day no observed effect concn was 0.013 mg/L, with the more sensitive parameters being reproductive rate and the appearance of first offspring.

3-Chloroaniline, which is the main metabolite of chloropropham, corresponded to about 50% of the applied dosage of chloropropham in the 2nd of 3rd successive lettuce cultures(1). After the 3rd culture, the amount of chloropropham and 3-chloroaniline increased lettuce, as well as soil(1).

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

MAY BE ABSORBED! Redness. Burning sensation. 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=108-42-9]

In a comprehensive survey of wastewater from 4,000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the U.S. EPA, 3-chloroaniline was identified in discharges of the following industrial category (positive occurrences, median concn in ug/L): organics and plastics (5; 96.7), soaps and detergents (1; 28.0), pharmaceuticals (6; 58.7), organic chemicals (3; 13.8), publicly owned treatment works (14; 2.6)(3). The highest effluent concn was 612 ug/L in the pharmaceutical industry(3). Unspecified isomers of chloroaniline have been detected in the effluent from the publicly owned treatment works (POTW) of Sauget, IL(1). 3-Chloroaniline has been qualitatively detected in effluent water concentrates collected in 1974 and 1975 from advanced waste treatment facilities in Pomona, CA(2).

The Koc of 3-chloroaniline is estimated as 250(SRC), using a log Kow of 1.88(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 3-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). In laboratory persistence studies using non-sterilized Hagerstown silty clay loam soil, 73% of applied 3-chloroaniline remained chemically bound to soil particles after 64 days of incubation(6). A related chemical, 2-chloroaniline, has 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 followed by oxidation of the product to give an amino-substituted quinone(7).

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, 3-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. m-chloroaniline is produced, as an intermediate or a final product, by process units covered under this subpart.

3-Chloroaniline was excreted /by rats/ in urine as glucuronides and sulfate esters of 4-hydroxy-3-chloroacetanilide (a major metabolite) and 2-hydroxy-5-chloroacetanilide (a minor metabolite).

...In male albino rats after a single oral dose /of 3-chloroaniline/ urine was collected and analyzed. ...TLC showed the presence of 2-amino-4-chlorophenol and 4-amino-2-chlorophenol. ...Acetyl phenols were also identified /as were/ glucuronides and sulfates of the phenols and their acetyl derivatives. ...2-Amino-6-chlorophenol was not found but traces of the glucuronide and sulfate were. ...

Metabolites identified following oral administration of 150 mg/kg in rats: 2-amino-4-chlorophenyl-beta-d-glucuronide, 4-amino-2-chloro phenyl-beta-d-glucuronide, 4-acetylamino-2-chlorophenyl-beta-d-glucuronide, 2-acetylamino-4-chlorophenyl-beta-d-glucuronide, 2-amino-4-chlorophenylsulfate, 4-amino-2-chlorophenylsulfate, 2-acetylamino-4-chlorophenylsulfate, and 4-acetylamino-2-chlorophenylsulfate.

High performance liquid chromatography was used to quantify the metabolism of free chlorpham and its metabolites in isolated rat hepatocyte incubations. ... 10 percent was metabolized to 3-chloroaniline which was broken down to 3-chloroacetanilide. ...

For more Metabolism/Metabolites (Complete) data for 3-CHLOROANILINE (6 total), please visit the HSDB record page.

Used as an intermediate to produce herbicides, pharmaceuticals, azo dyes, and pigments; [HSDB]

... Used as an intermediate for pesticides, pharmaceuticals, and dyes.

Chem int for the herbicide chlorpropham, m-chlorophenyl isocyanurate, pharmaceuticals, and azo dyes and pigments

Intermediate for azo dyes and pigments, insecticides, agricultural chemicals.

... Produced by low-pressure hydrogenation of 3-chloronitrobenzene in the liquid phase with noble metal and/or noble metal sulfide catalysts. The addition of metal oxides to the reaction helps avoid dehalogenation. The yield is approximately 98%.

... Catalytic hydrogenation of chloronitrobenzene.

... By reduction of chloronitrobenzene with NaHS.

All Other Basic Organic Chemical Manufacturing

Benzenamine, 3-chloro-: ACTIVE