Nitroanilin (o,m,p)

log Kow = 1.85

1.44

1.62

1.44 at 68 °F (USCG, 1999) - Denser than water; will sink

0.9015 at 25 °C/4 °C

1.44 g/cm³

0.9015 @25 °C

Yellow-orange crystals from boiling water

Orange-red needles

less than 1 mg/mL at 70.7 °F (NTP, 1992)

Soluble in ethanol; very soluble in ether, acetone, benzene, chloroform

Slightly sol in cold water; sol in hot water

In water, 1.47X10+3 mg/L at 30 °C

Solubility in water, g/100ml at 25 °C: 0.126

335 °F (NTP, 1992)

168 °C

168 °C

543 °F at 760 mmHg (NTP, 1992)

284 °C

284 °C

284.5 °C @760 [mm Hg]

160.7 °F (NTP, 1992)

71.0 °C

Heat of fusion at melting point = 16.1 kJ/mol

71 °C

72 °C

Danger

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

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

This chemical does not meet GHS hazard criteria for 0.4% (1 of 227) of reports.

Danger

H301 (97.4%): Toxic if swallowed [Danger Acute toxicity, oral]

Chemical: Benzenamine, 2-nitro-

Benzenamine, 2-nitro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, 2-nitro- 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: 28-06-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/13715

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

Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire. (USCG, 1999)

Combustible. Many reactions may cause fire or explosion. Finely dispersed particles form explosive mixtures in air.

SLIGHT, WHEN EXPOSED TO HEAT OR FLAME.

COMBUSTIBLE. IN PRESENCE OF MOISTURE CAUSES NITRATION OF ORG MATERIALS & MAY RESULT IN SPONTANEOUS IGNITION.

Process errors led to discharge of copious amt of nitrous fumes into glass reinforced plastic ventilation duct above diazotization vessel. On 2 occasions fires were caused in the duct by vigorous reaction of the dinitrogen tetraoxide with nitroaniline dusts in the duct. /Nitroaniline dust/

Inhalation or ingestion causes headache, nausea, methemo- globinemia, vomiting, weakness, and stupor; cyanosis caused by contact usually develops in 4-6 hrs.; prolonged and excessive exposure may also cause liver damage. Contact with eyes or skin causes irritation; continued exposure may cause same symptoms as inhalation or ingestion. (USCG, 1999)

Highly toxic; May be absorbed through skin; May induce methemoglobinemia and cyanosis; Prolonged exposure may cause damage to the liver; [Merck Index] Can induce methemoglobinemia; [ICSC] A skin, eye, nose, and throat irritant; [HSDB] An irritant; [MSDSonline]

European Chemicals Bureau; IUCLID Dataset, 2-Nitroaniline (CAS # 88-74-4) summarizes information provided to the EU by the European chemical industry as of 2000.

Organisation for Economic Cooperation and Development; Screening Information Data Set for 2-Nitroanilne, CAS #88-74-4 96 p. (November 2001) is an initial assessment report prepared by the sponsor country, France, for the 13th SIAM (Bern, Switzerland, 6-9 November 2001).

Santodonato J et al; Monographs on Human Exposure to Chemicals in the Workplace: Nitroanilines 1-26 (1985). This report summarizes and evaluates toxicologic information relevant to an occupational hazard assessment of nitroanilines, including chemical and physical properties, production and use, extent of occupational exposure, pharmacokinetics, animal carcinogenicity and mutagenicity, and epidemiological studies.

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

O-NITROANILINE may be sensitive to prolonged exposure to light. Mixtures of this chemical with magnesium are hypergolic on contact with nitric acid. It forms extremely explosive addition compounds with hexanitroethane. It has a vigorous reaction with sulfuric acid above 392 °F. It is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizers. (NTP, 1992)

Fire Extinguishing Agents: Water, foam, dry chemical, carbon dioxide (USCG, 1999)

Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position.

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Induce vomiting (ONLY IN CONSCIOUS PERSONS!). 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.

Extinguish with water, dry chemicals, foam or carbon dioxide.

FIGHT FIRES FROM EXPLOSION RESISTANT LOCATION. USE WATER FROM UNMANNED MONITORS OR HOSEHOLDERS TO KEEP FIRE-EXPOSED CONTAINERS COOL. ON FIRES IN WHICH CONTAINERS ARE NOT EXPOSED USE WATER SPRAY, CARBON DIOXIDE, DRY CHEM, OR FOAM.

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use water foam, dry chemical, or carbon dioxide. /Nitroanilines/

Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Nitroanilines/

1. Ventilate area of spill. 2. For small quantities, sweep onto paper or other suitable material, place in an appropriate container & burn in a safe place (such as a fume hood). Large quantities may be reclaimed; however, if this is not practical, dissolve in a flammable solvent (such as alcohol) & atomize in a suitable combustion chamber equipped with an appropriate effluent gas cleaning device.

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.

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: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder.

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.

Good ventilation in work areas or gas mask. Avoid direct contact by the personnels handling the substances. Sanitory work areas by daily cleansing is advised. ... Immediately remove the adherent substance as well as all clothing. Wash the contaminated surface of the body with soap and water, including ear canals and nail beds.

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.

Evacuation: If material leaking (not on fire) consider evacuation from downwind area based on amount of material spilled, location, and weather conditions. /Nitroanilines/

For more Preventive Measures (Complete) data for 2-NITROANILINE (6 total), please visit the HSDB record page.

LC50 Cyprinus carpia (/carp/, age 1 year, weight 23.8 g, length 11.6 cm) 16.2 mg/L/96 hr; semistatic, dechlorinated tap water with 21.45 mg/L chlorine; 15-18 °C, pH 7.0-7.5, dissolved oxygen 6.35 mg/L.

LC50 Carassius auratus (/goldfish/, weight 3.5 g, length 4.0 cm) 1.66 mg/L/48 hr; semistatic, freshwater; 20 °C, pH 7.5, dissolved oxygen 8.2 mg/L, hardness (CaCO3) 110 mg/L.

LC50 Carassius auratus (/goldfish/) 11.5 mg/L/48 hr. /Conditions of bioassay not specified/

LD50 Aeglaius phoeniceus (redwinged blackbird) oral 750 mg/kg

For more Ecotoxicity Values (Complete) data for 2-NITROANILINE (17 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 59(2), indicates that 2-nitroaniline is expected to have high mobility in soil(SRC). However, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3,4), suggesting that mobility may be much lower in some soils(SRC). Volatilization of 2-nitroaniline from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 5.9X10-8 atm-cu m/mole(5). 2-Nitroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.77X10-3 mm Hg(6). Degradation in a soil mineral salts suspension took greater than 64 days(7), indicating that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 59(2) indicates that 2-nitroaniline is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 5.9X10-8 atm-cu m/mole(4). According to a classification scheme(5), BCF values of <10(6,7) suggest bioconcentration in aquatic organisms is low(SRC). 2-Nitroaniline is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Aromatic amines react relatively rapidly in natural water with photochemically produced oxidants such as hydroxyl radicals and alkoxy radicals(8); half-lives of aniline are on the order of 30 hr of sunlight for hydroxyl radicals and 19 hr of sunlight for alkoxy radicals(8); reactions with 2-nitroaniline are likely to be somewhat slower due to the presence of the nitro function(SRC). 2-Nitroaniline had a biodegradation rate of 0.023/h in river water giving a half-life of 31 hours(9), indicating 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), 2-nitroaniline, which has a vapor pressure of 2.77X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 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 29 hours(SRC), calculated from its rate constant of 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2-Nitroaniline does absorb light at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

HUMAN HEALTH. The results of the published studies on 2-nitroaniline did not show significant increases of methemoglobin in animals except in the inhalation study. This difference with other isomers or inducers seems to be due to the difference of chemical reactivity of the nitro substitution in position 2 compared to other substitutions. 2-Nitroaniline is metabolised in vitro by rabbit liver microsomes to 4-amino-3-nitrophenol. 2-nitroaniline has been shown to have an oral LD50 value of 1838 mg/kg b/w in the rat, this is the only acute effect noted. It is not irritating to skin and to the eyes, and not sensitizing. In oral repeated administration a NOEL of 50 mg/kg bw/day was determined from a 9 weeks study. The major treatment -related effects are clinical signs, but not methemoglobinemia, and weight loss. In a vapor inhalation 28 day assay a NOAEL was determined at 10 mg/cu m in rats, due to slight methemoglobinemia and hematological effects seen at 90 mg/cu m. 2-Nitroaniline was shown to be non-mutagenic in relevant bacterial studies. Nonetheless, a weak mutagenic influence was reported in some studies in which tests were performed on S. typhimurium strains TA98 and TA1538 in the presence of Hamster S9 mix or with Flavin Mononucleotide activation. Investigations of general interaction with DNA on bacteria (E.coli) yielded negative results, as well as in vitro UDS tests and in vivo clastogenicity tests (micronucleus i.p.) or test on the alkaline elution behaviour of the DNA. In conclusion, 2-nitroaniline is not mutagenic. In reproduction and developmental toxicological studies, the substance caused neither teratogenic nor fertility effects, but did cause developmental effects due to pups lethality at 450 mg/kg bw /day where a maternal body weight decrease occurred. The NOAEL for developmental effects was 150 mg/kg bw/day and the maternal NOAEL was set at 50 mg /kg bw in a study according to OECD TG 422. ENVIRONMENT. 2-Nitroaniline has been found to be non-biodegradable, even in high inoculum concentration conditions. It therefore can be considered as persistent. The highest bioconcentration factor in fish was observed to be 8, leading to the conclusion that 2-nitroaniline does not significantly bioaccumulate. The most valid and lowest E(L)C 50 found were a LC 50 (96 hours) in Brachydanio rerio of 19.5 mg/l, an EC 50 (24 hours) in Daphnia magna of 8.3 mg/l and an EC50 (growth rate, 72 hours) in Selenastrum capricornutum was > 100 mg/l. The lowest result is the EC 50 (24 hours) in Daphnia magna. Using an extrapolation factor of 1000, a PNEC of 0.008 mg/l can be estimated for the aquatic compartment.

/AQUATIC SPECIES/ The LC50 (96 hr) values and the bioconcentration factors (BCF) for nine anilines (aniline; 2-, 3-, 4-chloroaniline; 2-, 3-, 4-nitroaniline; 2,4- and 3,4-dichloroaniline) in the zebrafish (Brachydanio rerio) were determined. Biotransformation products of anilines in the zebrafish were analyzed by HPLC. The aim of the investigations was to find relationships between accumulation/elimination/metabolism and toxicity on the one hand and between chemical structure and biotransformation on the other. ... A good correlation of log BCF and of log Pow with log LC50 /was found/. This concurs with the assumption that the internal dose determines the toxicological effect. All anilines investigated, with the exception of 2- and 4-nitroaniline, were transformed into the corresponding acetanilides. The toxicity of the compounds was not altered by biotransformation. ...

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

MAY BE ABSORBED! Further see Inhalation.

Further see Inhalation.

An unspecified isomer of nitroaniline was qualitatively detected in wastewater effluents from publicly-owned treatment works in Danville and Sauget, IL(1). 2-Nitroaniline was detected in municipal landfill leachate or groundwater plume at a concentration range of 180 mg/L at an unspecified site(2). Nitroaniline has been formed as a product during both the aerobic and anaerobic incubation of dinitrobenzene in sewage(3).

Consider the points of attack (blood, heart, lungs and liver) in preplacement and periodic physical examinations. /4-Nitroaniline/

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.

The log Koc of 2-nitroaniline was measured as 1.77 giving a Koc of 59(1). According to a classification scheme(2), this Koc value suggests that 2-nitroaniline is expected to have high mobility in soil. 2-Nitroaniline was found to have a Kd value of 8.4 L/kg in homoionic K+ Montmorillonite type soil(3). However, anilines are expected to bind strongly to humus or organic matter in soils due to high reactivity of the aromatic amine group(4,5), suggesting that mobility may be much lower in some soils(SRC).

Teratogenicity was evaluated in groups of pregnant Sprague-Dawley rats (25/group) receiving orthonitroaniline, orally by gavage, at concentrations of 0, 100, 300 or 600 mg/kg/day on days 6 through 15 of gestation Maternal toxicity was evident by statistical differences between dosed groups and controls for: number of cases of piloerections (mid and high dose groups), mean maternal body weights (mid and high dose groups) and food consumption (all treatment groups). Pregnancy rate and the number of live and dead fetuses, early and late resorptions, total nidations and corpora lutea were comparable for all groups. No meaningful differences in the total number of litters of fetuses exhibiting malformations was evident. However, one fetus in each of two litters at the 600 mg/kg level exhibited partial situs inversus and similar heart malformations.

The mutagenicity of ortho-nitroaniline was evaluated in Salmonella tester strains TA98, TA100, TA1535 and TA1537 (Ames Test), both in the presence and absence of added rat and mouse S-9 metabolic activation. Based on preliminary toxicity determinations, ortho-nitroaniline, was tested at concentrations up to 1.5 mg/plate using the plate incorporation technique. Ortho-nitroaniline did not cause a positive response in any of the tester strains with or without metabolic activation.

The mutagenicity of ortho-nitroaniline was evaluated in Salmonella tester strains TA98, TA100, TA1535 and TA1537 (Ames Test), both in the presence and absence of added rat and mouse S-9 metabolic activation. Based on preliminary toxicity determinations, ortho-nitroaniline, was tested at concentrations up to 1.5mg/plate using the plate incorporation technique. Ortho-nitroaniline did not cause a positive response in any of the tester strains with or without metabolic activation.

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

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

THE RELATIVE MUTAGENIC ACTIVITIES OF AMINOANILINES HAVE BEEN ATTEMPTED TO BE RELATED TO PARAMETERS REFLECTING POTENTIAL FOR N-HYDROXYLATION AND STABILITY OF THE ARYLNITRENIUM IONS. THE NITRO GROUPS DEACTIVATE THE AMINE GROUP N-HYDROXYLATION AND THE EPOXIDATION, & NO ACTIVE PRODUCTS FROM CYTOCHROME P450 WOULD BE PREDICTED. THE ACTIVITY OF THE NITRO DERIVATIVES IS PRESUMED TO BE DUE TO TRANSFORMATION OF THE NITRO GROUP ITSELF TO AN ACTIVE MUTAGENIC SPECIES BY OTHER ENZYME SYSTEMS. /AMINOANILINES/

The metabolism of radiolabeled dinitrobenzene isomers was compared in hepatocytes and hepatic subcellular fractions isolated from male rats. Under aerobic conditions, reduction was the major metabolic pathway for m-dinitrobenzene and p-dinitrobenzene in hepatocytes with m-nitroaniline and p-nitroaniline accounting for 74.0 and 81.0% respectively, of the radioactivity present after a 30 min incubation. The major metabolite of o-nitrobenzene in similar incubations was S-(2-nitrophenyl)glutathione which represented 48.1% of the total radioactivity. o-Nitroaniline accounted for 29.5% of the radioactivity.

Used to make azo dyes and pigments, vat dyes, photographic antifogging agents, coccidiostats, and ortho-phenylenediamine; [HSDB] Used to make benzotriazoles, cutting fluids, and pharmaceuticals; [SIDSUNEP]

CHEM INT FOR CI PIGMENT YELLOW 5, ORANGE 2, YELLOW 7, VAT RED 15, VAT ORANGE 7, CI PIGMENT ORANGE 43, VAT RED 14, DISPERSE YELLOW 10.

Dye intermediate, synthesis of photographic antifogging agent, ortho-phenylenediamine, coccidiostats.

2-Nitroaniline is used as a diazo component (Fast Orange GR Base) in azo dyes and pigments (e.g., C.I. Disperse Yellow 10 and C.I. Pigment Yellow 5) and as an intermediate for vat dyes (e.g., C.I. Vat Red 14).

2023: 550,000 - <1,000,000 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 G

(1975) PROBABLY GREATER THAN 4.54X10+5 G

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#2865]

Benzenamine, 2-nitro- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

REACTION OF 1-CHLORO-2-NITROBENZENE WITH AMMONIA.

... From o-Dinitrobenzene; ... From o-Nitroaniline-p-Sulfonic acid; ... From PSI-o-Dinitrobenzene.

From aniline by nitration after acetylation, with subsequent removal of the acetyl group by hydrolysis; from o-dinitrosobenzene.

2-Chloronitrobenzene is heated with excess (10 mol/mol) strong aqueous ammonia in an autoclave. The temperature is gradually increased to 180 °C over 4 hr and held there for 5 hr more. The pressure builds up to around 4 MPa and is released to an ammonia recycle loop before the product is isolated by filtration and washing. The reaction is extremely exothermic (delta H= -168 kJ/mol), and too rapid heating or inadequate temperature control can result in a runaway reaction.

Paint and Coating Manufacturing

Benzenamine, 2-nitro-: ACTIVE