4-Chloro-2-nitroaniline

Orange crystals

Dark orange-yellow prisms from dil alc

less than 1 mg/mL at 72 °F (NTP, 1992)

Very soluble in ethanol, ether, acetic acid; slightly soluble in acetone, ligand

Insoluble in water, methanol, and ether

In water, 5,003 mg/L at 25 °C

241 to 243 °F (NTP, 1992)

116.5 °C

0.000485 [mmHg]

4.85X10-4 mm Hg at 25 °C (wat)

4-chloro-2-nitroaniline is a bright orange powder. (NTP, 1992)

Orange solid; [Hawley] Orange powder; [MSDSonline]

Positive

2.32

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Danger

H300 (99.4%): Fatal if swallowed [Danger Acute toxicity, oral]

P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P319, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 179 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

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

Chemical: Benzenamine, 4-chloro-2-nitro-

Status: Active Update: 14-05-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/7915

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

A mutagen; Acts as general anesthetic in lethal-dose feeding studies of guinea pigs; [RTECS] Emergency treatment: Methemoglobinemia; May caused severe damage to eyes; [HSDB] An irritant; May induce methemoglobinemia; May be absorbed through skin; [MSDSonline]

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importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies.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, 4-chloro-2-nitro- is included on this list. Effective date 10/4/82; Sunset date 10/4/92.

/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. /Chloronitroanilines/

/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. /Chloronitroanilines/

/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. /Chloronitroanilines/

/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. /Chloronitroanilines/

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

Acute Tox. 2 (99.4%)

Acute toxicity (ingestion) - category 4

Specific target organ toxicity - Repeated exposure - Category 2 (blood system)

Self-reactive substances and mixtures - Type G

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.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources.

Suitable extinguishing media: Use dry chemical, CO2, water spray or "alcohol" foam. As in any fire, wear self-contained breathing apparatus pressure-demand, MSHA/NIOSH (approved or equivalent) and full protective gear. Water mist may be used to cool closed containers.

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, you should dampen the solid spill material with alcohol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with alcohol 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 alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminate 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.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Do not use water.

Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment.

Ensure adequate ventilation. Handle in accordance with good industrial hygiene and safety practice.

Eye contact: In the case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Ingestion: Do not induce vomiting without medical advice. Never give anything by mouth to an unconscious person. Consult a physician.

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)

Personnel protection: ... Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective clothing Do not handle broken packages unless wearing appropriate personal protective equipment.

PERSONAL PROTECTIVE EQUIPMENT. Respiratory protection: Breathing apparatus only if aerosol or dust is formed. Hand protection: PVC or other plastic material gloves. Skin and body protection: Usual safety precautions while handling the product will provide adequate protection against this potential effect. Eye protection: Safety glasses with side-shields.

LC50; Species: Daphnia magna (Water flea, age 6-24 hr); Conditions: freshwater, static, 20 °C, pH > or =7.0; Concentration: 3700 ug/L for 24 hr

LC50; Species: Daphnia magna (Water flea, age 6-24 hr); Conditions: freshwater, static, 20 °C, pH > or =7.0; Concentration: 3200 ug/L for 48 hr (95% confidence interval: 2900-3500 ug/L)

EC50; Photobacterium phosphorem (19.8 ug/L);Condition: 15 degree C) for 30 min /Conditions of bioassay not specified in source examined/

EC50; Water flea (3.2 mg/L) for 48 hr /Conditions of bioassay not specified in source examined/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 720(SRC), determined from a log Kow of 2.72(2) and a regression-derived equation(3), indicates that 4-chloro-2-nitroaniline is expected to adsorb to suspended solids and sediment(SRC). Volatilization of 4-chloro-2-nitroaniline from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(4). 4-Chloro-2-nitroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.8X10-4 mm Hg(SRC), determined from a fragment constant method(5). A 0% theoretical BOD using an activated sludge inoculum and the Japanese MITI test(6) indicates that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 720(SRC), determined from a log Kow of 2.72(2) and a regression-derived equation(3), indicates that 4-chloro-2-nitroaniline is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.2X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), BCF values of 7.5-13.4(6), suggest bioconcentration in aquatic organisms is low(SRC). A 0% theoretical BOD using an activated sludge inoculum and the Japanese MITI test(6) indicates that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-chloro-2-nitroaniline, which has an estimated vapor pressure of 4.8X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 4-chloro-2-nitroaniline 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 4 days(SRC), calculated from its rate constant of 3.9X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). The compound contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

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=89-63-4]

4-Chloro-2-nitroaniline was identified in one industrial wastewater extract of an organic and plastic industry at a concentration of 246 ng/uL extract(1). 4-Chloro-2-nitroaniline was identified at a concentration of 11 ug/mL in hazardous waste incineration effluents from four different test sites(2). 4-Chloro-2-nitroaniline was qualitatively detected in advanced waste treatment concentrate from Lake Tahoe, CA on October 24, 1974(3).

The Koc of 4-chloro-2-nitroaniline is estimated as 720(SRC), using a log Kow of 2.72(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 4-chloro-2-nitroaniline is expected to have low mobility in soil. Anilines 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 log Koc of 4-chloro-2-nitroaniline was measured as 2.30 in Yangtze river sediment (37.1% sand, 49.3% silt, 13.6% clay, 1.28% organic carbon, pH 7.44)(6). The log Koc was also measured as 3.68 in modified clay(7). These values give Koc values of 200 and 4800, respectively(SRC).

/SIGNS AND SYMPTOMS/ Chronic toxicity: Chronic exposure may cause nausea and vomiting, higher exposure causes unconsciousness. Local effects: Symptoms of overexposure may be headache, dizziness, tiredness, nausea and vomiting. Specific effects: May include moderate to severe erythema (redness) and moderate edema (raised skin), nausea, vomiting, headache.

/OTHER TOXICITY INFORMATION/ Harmful by inhalation, in contact with skin and if swallowed. ... Risk of serious damage to eyes

A 6 week bioconcentration study obtained BCF values of 7.5-13.2 and 8.0-13.4 in carp (Cyprinus carpio) for concentrations of 4-chloro-2-nitroaniline of 100 and 10 ppb, respectively(1). According to a classification scheme(2), these BCF values suggest bioconcentration in aquatic organisms is low(SRC).

The Henry's Law constant for 4-chloro-2-nitroaniline is estimated as 1.2X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 4-chloro-2-nitroaniline is expected to be essentially nonvolatile from water surfaces(2). 4-Chloro-2-nitroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.8X10-4 mm Hg(SRC), determined from a fragment constant method(3).

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, 4-chloro-2-nitro- is included on this list. Effective date 10/4/82; Sunset date 10/4/92.

The disposition and metabolism of 14C-labeled 4-chloro-2-nitroaniline (CNA) was studied in male F344 rats following oral or intravenous (iv) administration...The whole-body half-life of CNA in the rat was approximately 1 hr, and clearance of radioactivity from the body was near complete in 3 d...

The disposition and metabolism of 14C-labeled 4-chloro-2-nitroaniline (CNA) was studied in male F344 rats following oral or intravenous (iv) administration. The gastrointestinal absorption of CNA was found to be near complete and was not affected by the dose in the range studied (0.788-78.8 mumol/kg). Following either oral or iv administration, CNA was rapidly distributed throughout the tissues and showed no marked affinity for any particular tissue. [14C]CNA was rapidly cleared by metabolism and excretion in urine and to a lesser extent in feces. The whole-body half-life of CNA in the rat was approximately 1 hr, and clearance of radioactivity from the body was near complete in 3 d. The known carcinogen and potential metabolite of CNA, 4-chloro-o-phenylenediamine, was not detected in rat tissues or excreta following administration of CNA. Approximately 70% of the dose was detected in urine as a sulfate conjugate of a single metabolite of CNA. The remainder of the dose was excreted in the form of seven additional metabolites and a trace of the parent compound. CNA-derived radioactivity had little potential for bioaccumulation, and there was no evidence for saturation of any mechanism involved in the absorption, distribution, metabolism, or excretion of CNA in the dose range studied.

The disposition and metabolism of 14C-labeled 4-chloro-2-nitroaniline (CNA) was studied in male F344 rats following oral or intravenous (iv) administration. The gastrointestinal absorption of CNA was found to be near complete and was not affected by the dose in the range studied (0.788-78.8 mumol/kg). Following either oral or iv administration, CNA was rapidly distributed throughout the tissues and showed no marked affinity for any particular tissue. [14C]CNA was rapidly cleared by metabolism and excretion in urine and to a lesser extent in feces...

Used as a dye and pigment intermediate; [Hawley]

Dye and pigment intermediate

CHEM INT FOR TWO MAJOR C.I. PIGMENTS-YELLOWS 73 AND 3, FOR OTHER PIGMENTS (EG, C.I. PIGMENT RED 6)

4-Chloro-2-nitroaniline is used as a diazo component (Red 3GL Base) in C.I. Pigment Yellow 3 and C.I. Pigment Red 6, for example.

(1977) 1.13X10+8 G (PRINCPL CUSTMS DISTS)

(1979) 9.79X10+7 G (PRINCPL CUSTMS DISTS)

(1976) 9.57X10+7 G (SALT)

(1979) PROBABLY GREATER THAN 4.54X10+6 G

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5247]

... Produced by selective ammonolysis of 1,4-dichloro-2-nitrobenzene ...

1,4-Dichloro-2-nitrobenzene ... is aminated at 165 °C.