4-Chloro-2-nitroaniline

172.56900

172.57

201-925-4

1929LY233C

3546

2237

DTXSID4030384

Orange crystals|Dark orange-yellow prisms from dil alc

29214210

71.84000

2.93480

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

1.494g/cm3

116-117 °C

135-137 °C @ Press: 2 x 10^-4 Torr

191ºC

1.646

H2O: INsoluble

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

4.85X10-4 mm Hg at 25 deg C (wat)

Henry's Law constant = 1.22X10-7 atm-cu m/mol at 25 °C (est)

pKa = -1.02 (conjugate acid)

Hydroxyl radical reaction rate constant = 3.93X10-12 cu cm/molec-sec at 25 °C (est)

Insoluble in water.

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

4-CHLORO-2-NITROANILINE forms explosive products on reaction with nitric acid. Can react with oxidizing agents. (NTP, 1992)

III

6.1

UN 2237

2

R26/27/28; R33; R51/53

S28-S36/37-S45-S61

BX1575000

T+; N

Stable. Combustible. Incompatible with strong oxidizing agents.

P260-P264-P273-P280-P284-P301 + P310

H300 + H310 + H330-H373-H411

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.

In a large scale-up of the method for preparing 4-chloro-2,6-dinitroaniline by reacting nitric acid with 4-chloro-2-nitroaniline, an unexpected strong evolution of heat was experienced. The exotherm was found due to the simultaneous formation of two explosive products: the isomer 2-chloro-4,6-dinitroaniline & also 4-chloro-3,6-dinitrophenyldiazonium-2-oxide.

This compound is probably combustible. (NTP, 1992)

|Danger|H300 (99.48%): Fatal if swallowed [Danger Acute toxicity, oral]|P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, P330, P361, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 192 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P264, P270, P273, P280, P301+P312, P302+P352, P314, P321, P330, P332+P313, P362, P391, and P501|H373: Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]|P260, P314, and P501

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: 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. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck 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, 2016)

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. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

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.

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.

Prevent product from entering drains. Sweep up and shovel into suitable containers for disposal.

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.

/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.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

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).

LD50 Rat oral 400 mg/kg|LD50 Mouse oral 800 mg/kg

Routine checking of lips, tongue and nail beds of exposed personnel for signs of cyanosis. /Protect/ from exposure those individuals with anemia, cardiovascular or pulmonary diseases.

4-Chloro-2-nitroaniline's production and use as a dye and pigment intermediate(1) may result in its release to the environment through various waste streams(SRC).

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 rate constant for the vapor-phase reaction of 4-chloro-2-nitroaniline with photochemically-produced hydroxyl radicals has been estimated as 3.9X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 4-Chloro-2-nitroaniline is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). The compound contains chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

10.96|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 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).

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).

DRINKING WATER: 4-Chloro-2-nitroaniline was qualitatively detected in drinking water concentrate from Cincinnati, Ohio on October 17, 1978(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 17,827 workers (16,443 of these are female) are potentially exposed to 4-chloro-2-nitroaniline in the US(1). Occupational exposure to 4-chloro-2-nitroaniline may occur through dermal contact with this compound at workplaces where 4-chloro-2-nitroaniline is produced or used(SRC).

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 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.

0.11 Days|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...

SYMPTOMS: Exposure to this material can cause local irritation, headache, cyanosis, jaundice, methemoglobinemia, weight loss, anemia, weakness and irritability. ACUTE/CHRONIC HAZARDS: This chemical is a skin irritant and an allergen. It can be absorbed through the skin and upon inhalation of dust. Toxic fumes are evolved when this material is heated to decomposition or upon contact with acid or acid fumes. (NTP, 1992)

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)

/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

4-chloro-2-nitroaniline

ESSENTIALLY 100% AS A CHEMICAL INTERMEDIATE

Synthetic dye and pigment manufacturing|Benzenamine, 4-chloro-2-nitro-: ACTIVE

HPLC METHOD WAS DEVELOPED FOR THE DETECTON OF SUB-NG QUANTITIES OF HALOGENATED ANILINE DERIVATIVES. /P-CHLOROANILINE/|p-Chloroaniline was determined in chlorhexidine gluconate by spectrophotometry. Absorbance was measured at 455 nm. /p-Chloroaniline/|A method is described for determining 4-chloroaniline in the ppm range using ion-pairing, reversed-phase high pressure liquid chromatographic technique & uv detection at 260 nm. /p-Chloroaniline/|Method 8270: Gas Chromatography/Mass Spectrometry for Semivolatile Organics, Capillary Column Technique. This gas chromatography/mass spectrometry method is used to determine the concentration of semivolatile organic compounds in extracts prepared from all types of solid waste matrices, soils, and ground water. The practical quantitation limit for determining an individual compound is approximately 1 mg/kg (wet weight) for soil/sediment samples, 1-200 mg/kg for wastes, and 10 ug/l for ground water. This method is applicable to quantify most neutral, acidic, and basic organic compounds that are soluble in methylene chloride, including the title compound, and are capable of being eluted without derivatization as sharp peaks from a 30 m by 0.25 mm ID (or 0.32 mm ID) 1 um film thickness silicon-coated fused silica capillary column (J&W Scientific DB-5 or equivalent). A representative sample is collected in a glass container equipped with a Teflon-lined cap. Care is taken to avoid sample contact with any plastic. Under the prescribed conditions, 4-chloroaniline has a retention time of 10.08 min. /p-Chloroaniline/|For more Analytic Laboratory Methods (Complete) data for 4-CHLORO-2-NITROANILINE (6 total), please visit the HSDB record page.

4-CHLOROANILINE WAS DETERMINED IN URINE BY HPLC WITH ELECTROCHEMICAL DETECTOR. /P-CHLOROANILINE/