Nitroanilin (p)

Nitrogen Compounds -> Nitroanilines

Mutagens

Textile

log Kow = 1.39

2.66

1.46

Faint ammonia; slightly pungent

Odorless

Slight ammonia-like odor.

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

1.424 at 20 °C/4 °C

1.4 g/cm³

1.42

1.424 @ 20°C

1.42

Pale yellow monoclinic crystals from water

Bright yellow powder

Bright yellow, crystalline powder.

less than 0.1 mg/mL at 70 °F (NTP, 1992)

Very soluble in methanol; soluble in ethanol, ether, acetone, chloroform, toluene; slightly soluble in benzene, deuterated DMSO

1 g/45 mL boiling water; 1 g/25 mL alcohol; 1 g/30 mL ether

0.08 g/100 g water at 18.5 °C.

In water, 390 ppm at 20 °C

For more Solubility (Complete) data for 4-NITROANILINE (7 total), please visit the HSDB record page.

390 °F (NTP, 1992)

199 °C

329 °F (OPEN CUP) (MOLTEN SOLID)

199 °C (closed cup)

199 °C

390 °F

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)

Danger

H301+H311+H331 (36.1%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

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)

Chemical: Benzenamine, 4-nitro-

Regulation (EC) No 1831/2003 (amended)

Benzenamine, 4-nitro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, 4-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)

T - indicates a substance that is the subject of a final TSCA section 4 test rule.

Status: Active Update: 22-08-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/5825

4-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.

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

Combustible 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.

Inhalation or ingestion causes headache, drowsiness, shortness of breath, nausea, methemoglobinemia, and unconsciousness; fingernails, lips, and ears become bluish; prolonged and excessive exposures may also cause liver damage. Contact with eyes causes irritation and possible corneal damage. Contact with skin causes irritation; continued exposure may cause same symptoms as inhalation or ingestion. (USCG, 1999)

Can cause severe methemoglobinemia in the workplace; Chronic exposure can cause anemia, jaundice, and liver injury; Listed in a table of Industrial Chemicals for Which Methemoglobin Formation is the Principal Cause of Toxicity; [ACGIH] A mild eye irritant; May induce methemoglobinemia; [ICSC]

European Chemicals Bureau; IUCLID Dataset, 4-Nitroaniline (CAS # 100-01-6). Summary of information provided to the EU by the European chemical industry as of 2000.

Rickert DE; Toxicity of Nitroaromatic Compounds 1-295 Hemisphere Publising Corp (1985). Papers presented in 1982, cover: occurrence and uses of nitroaromatic compounds in industry; carcinogenicity, mutagenicity and teratogenicity of the compounds; interaction of the compounds with DNA; sex, strain and species differences in rodent response to nitrobenzene; mammalian and bacterial metabolism of nitroaromatics; skin penetration; absence fo reduced fertility among chemical plant workers exposed to dinitrotoluene and toluene G diamine; subclinical effects of trinitrotoluene; risk assessment.

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.

x[DHHS/NTP; Toxicology & Carcinogenesis Studies of p-Nitroaniline in B6C3F1 Mice (Gavage Studies) Technical Report Series No. 418 (1993) NIH Publication No. 93-3149]

Fire Extinguishing Agents: Water, foam, dry chemical or 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.

(General first aid procedures)

This chemical is a combustible solid. Use dry chemical, carbon dioxide, water spray, or alcohol foam extinguishers. Poisonous gases including sulfur dioxide and nitrogen oxides are produced in fire. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. If employees are expected to fight fires, they must be trained and equipped in OSHA 1910.156.

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.

Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Use HEPA vacuum or wet method to reduce dust during clean-up. Do not dry sweep. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area after clean-up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable.

Effectiveness of purification of p-nitroaniline waste water contaminants was increased by using pseudomonas fluorescens 5/7 in aerating purifiers with the addition of nutrient salts in waste waters.

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.

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P077, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

Incineration (1800 °F, 2.0 seconds method) with scrubbing for NOx abatement. ...

A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.

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. Wash away remainder with plenty of water.

Employees should wash immediately with soap when skin is wet or contaminated & daily at the end of each work shift. Work clothing should be changed daily if ... contaminated. Remove non-impervious clothing immediately if wet or contaminated. Provide emergency showers.

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.

Ample ventilation of work area or with piped air respirator. Extreme sanitary and clean work area and of the personnel is necessary.

Eating and smoking should not be permitted in areas where liquid 4-nitroaniline is handled, processed, or stored.

For more Preventive Measures (Complete) data for 4-NITROANILINE (15 total), please visit the HSDB record page.

EC50 Chlorella vulgaris (Algae) 350.14 mg/L/6 hr; biomass.

LC50 Leuciscus idus (/Orfe/) 35 mg/L/48 hr; static, freshwater.

LC50; Species: Danio rerio (Zebra danio, age 3 months, weight 200-350 mg); Conditions: freshwater, renewal, 26.5 °C, pH 8.6, dissolved oxygen 85%; Concentration: 908 umol/L for 96 hr

LC50; Species: Daphnia magna (Water flea age < or =24 hr); Conditions: freshwater, static, 20-22 °C, pH 7.6-7.7, hardness 16 dH; Concentration: 24 mg/L for 24 hr

For more Ecotoxicity Values (Complete) data for 4-NITROANILINE (10 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 54-87(2-6), indicate that 4-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(7,8), suggesting that mobility may be much lower in some soils(SRC).Volatilization of 4-nitroaniline from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 1.26X10-9 atm-cu m/mole(9). 4-Nitroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.2X10-6 mm Hg(10). A 0% theoretical biodegradation using the Japanese MITI test(11) indicates that biodegradtion is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 54-87(2-6), indicate that 4-nitroaniline is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(7) based upon a Henry's Law constant of 1.26X10-9 atm-cu m/mole(8). 4-Nitroaniline is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(9). Aromatic amines react relatively rapidly in natural water with photochemically produced oxidants such as hydroxyl radicals and alkoxy radicals(9); half-lives of aniline are on the order of 30 hr of sunlight for hydroxyl radicals and 19 hr of sunlight for peroxy radicals(9); reactions with 4-nitroaniline are likely to be somewhat slower due to the presence of the nitro function(SRC). According to a classification scheme(9), BCF values of <10(10,11) suggest bioconcentration in aquatic organisms is low(SRC). A biodegradation rate of 0.025/h in river water giving a half-life of 31 hours(12) suggests 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-nitroaniline, which has a vapor pressure of 3.2X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 4-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). Particulate-phase 4-nitroaniline may be removed from the air by wet or dry deposition(SRC). 4-Nitroaniline does absorb light at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

/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. ...

/OTHER TERRESTRIAL SPECIES/ Benzamines are the major aromatic amines used in industry and can also be released from azo dyes, which are widely used in the textile, paper-making, and food industries. The toxicity of 10 benzamines was tested by the well diffusion assay technique against 18 common bacterial species including the nitrogen-fixing bacterium Azotobacter vinelandii. p-Phenylenediamine was found to be inhibitory to the growth of Aeromonas hydrophila and Pseudomonas fluorescens. o-Phenylenediamine was inhibitory to Escherichia coli, Klebsiella pnemoniae, Salmonella enteritidis, and Shigella sonnei. 2,5-Diaminotoluene was inhibitory to the growth of P. fluorescens and Streptococcus mitis. The growth of A. vinelandii was inhibited by p-phenylenediamine and 2,5-diaminotoluene in the well diffusion assay. p-Nitroaniline was also found to be inhibitory to the growth of A. vinelandii in Burk's nitrogen-free medium. The nitrogenase activity of A. vinelandii was inhibited by p-phenylenediamine, 2,5-diaminotoluene, p-nitroaniline, 2-nitro-p-phenylenediamine, 3-nitro-o-phenylenediamine, and 4-nitro-o-phenylenediamine. Because many of these organisms are common soil and aquatic bacteria, the accumulation of these benzamine compounds in the environment may have an adverse impact on soil biochemical activities.

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

MAY BE ABSORBED! Further see Inhalation.

Redness. Pain.

Further see Inhalation.

irritation nose, throat; cyanosis, ataxia; tachycardia, tachypnea; dyspnea (breathing difficulty); irritability; vomiting, diarrhea; convulsions; resp arrest; anemia; methemoglobinemia; jaundice

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=100-01-6]

Raw wastewater collected from a US dye manufacturing plant on the Black River, South Carolina in July 1976 contained 270 ppb nitroaniline (isomers unspecified); the final treated effluent contained no detectable levels of nitroaniline(1). 4-Nitroaniline was qualitatively detected in a stack effluent from a hazardous waste incinerator(2). 4-Nitroaniline has been detected in waste landfill leachates from various locations throughout the United States, however, concentrations were not given(3). 4-Nitroaniline was tested in tire leachate water form tires used as artificial reefs in canals but not detected at a detection limit of 1.0 ug/L(4).

Whole Blood (chemical/metabolite) Methemoglobin; Complete Blood Count; Liver Function Tests

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

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-Nitroaniline has measured log Koc values of 1.78(1) and 1.88(2) and log Kom values of 1.49(3) and 1.64(4). These values correspond to Koc values of 60, 76, 54 and 75, respectively. 4-Nitroaniline has also been observed to have a Koc of 87(5). According to a classification scheme(6), these Koc values suggest that 4-nitroaniline is expected to have high mobility in soil. 4-Nitroaniline was found to have a Kd value of 13.5 L/kg in homoionic K+ Montmorillonite type soil(7). However, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(8,9), suggesting that mobility may be much lower in some soils(SRC). 4-Nitroaniline had small and scattered amounts of irreversible binding over a 20 hour experiment(10).

P077; As stipulated in 40 CFR 261.33, when p-Nitroaniline, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

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. p-Nitroaniline is included on this list. Effective date 3/11/94; Sunset date 6/30/98.

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

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

... To assess further the role of the 4-substituent in methaemoglobinaemia, the toxicity of a series of 4-substituted aniline derivatives was also studied. Of the anilines studied, 4-nitroaniline caused the most methemoglobin (36.5 +/- 8.0%), while aniline caused the least (0.3 +/- 0.5%). Overall, there was a significant correlation (r2 = 0.83) between the hemotoxicity and the Hammett constant, sigma(p), suggesting that it is the electron-withdrawing properties of the substituent that influence the methemoglobin formation. ...

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. Both chloro and the nitro groups deactivate the amine group to n-hydroxylation and the ring to 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/

Given orally or ip in doses of 20-40 mg/kg in rats, analysis of 24-hr urine samples showed that 4-nitroaniline was excreted partly unchanged & also as 4-phenylenediamine & 2-amino-5-nitrophenol...

The principal rat liver microsomal metabolite of 4-nitroaniline was isolated by high performance liquid chromatography and characterized as 2-amino-5-nitrophenol. Pretreatment of rats with phenobarbital and 3-methylcholanthrene increased the rate of conversion of 4-nitroaniline to 2-amino-5-nitrophenol by 2- and 4-fold, respectively.

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-minute 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.

14(C) p-nitroaniline was rapidly cleared by metabolism to 9 metabolites which were excreted primarily in the urine and to a lesser extent in the feces. Most (56%) of the urinary radioactivity was in the form of sulfate conjugates of 2 metabolites of p-nitroaniline.

It is absorbed through the skin.

... Absorbed ... by inhalation of dust or vapor.

The disposition of 14(C)-labeled p-nitroaniline was studied in male rats following oral or iv admin. The clearance of 14(C) p-nitroaniline-derived radioactivity from various tissues was rapid and followed a 2-component decay curve. The whole-body half-life of p-nitroaniline was approximately 1 hr. Within 3 days, clearance of p-nitroaniline-derived radioactivity from the body was almost complete. 14(C) p-nitroaniline was rapidly cleared by metabolism to 9 metabolites which were excreted primarily in the urine and to a lesser extent in the feces. Most (56%) of the urinary radioactivity was in the form of sulfate conjugates of 2 metabolites of p-nitroaniline.

The percutaneous absorption of nitrobenzene, p-nitroaniline, 2,4-dinitrochlorobenzene, 2-nitro-p-phenylenediamine, and 4-amino-2-nitrophenol was studied in vivo and in vitro. The compounds were applied to shaved abdominal skins of Rhesus-monkeys at a concentration of 4 ug/sq cm. Five day urine samples were collected and analyzed for the compounds. Radiolabeled nitrobenzene, p-nitroaniline, 2-4-dinitrochlorobenzene, 2-nitro-p-phenylenediamine, or 4-amino-2-nitrophenol were applied to excised human skin at a dose of 4 ug/sq cm using a diffusion cell technique. Penetration of radioactivity through the skin was monitored for the next 24 hours. The compounds rapidly penetrated excised human skin, the greatest penetration occurring in the first 2 hours after exposure. The ability of the compounds to penetrate human skin ranked in decreasing order of permeability and corrected for evaporation was 4-amino-2-nitrophenol, nitrobenzene, p-nitroaniline, 2,4-dinitrochlorobenzene, and 2-nitro-p-phenylenediamine. The corresponding rank for penetration of monkey skin was 4-amino-2-nitrophenol, p-nitroaniline, 2,4-dinitrochlorobenzene, 2-nitro-p-phenylenediamine, and nitrobenzene.

Used in the production of dyes, antioxidants, gasoline gum inhibitors, and corrosion inhibitors; [ACGIH]

p-Nitroaniline is used as an intermediate in the manufacture of dyes, antioxidants, pharmaceuticals, and pesticides.

MEDICATION (VET)

CHEM INT FOR ANTIOXIDANTS, DYES, PIGMENTS, GASOLINE GUM INHIBITORS

Dye intermediate, especially for p-nitraniline red ...

For more Uses (Complete) data for 4-NITROANILINE (6 total), please visit the HSDB record page.

(1972) 1.1X10+7 G (PRINCPL CUSTMS DISTS)

(1975) 1.23X10+9 G

(1983) 5.72X1O+8 g

2023: 250,000 - <400,000 lb

(1973) 4.77X10+9 G (DEMAND EST)

(1975) 3.93X10+9 G

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#2903]

Benzenamine, 4-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).

AMMONOLYSIS OF P-NITROCHLOROBENZENE; OR BY NITRATION OF ACETANILIDE FOLLOWED BY HYDROLYSIS.

FROM ACETANILIDE; ... BY SCHMIDT REACTION.

PREPARED FROM THE REACTION OF GAMMA-GLUTAMYL-P-NITROANILIDE WITH GAMMA-GLUTAMYL TRANSPEPTIDASE.

Batchwise amination of 4-chloronitrobenzene is carried out at 195 °C (4.5 MPa) in a process similar to that for 2-nitroaniline. In the alternative continuous process, molten 4-chloronitrobenzene and 40% ammonia liquor in a molar ratio of 1:17 are pumped at 20 MPa through a steel reaction coil held at 237-240 °C by oil bath heating. Inflow is controlled to give a contact time of ca. 10 min, and outflow is directed into an expansion chamber with a tangential flow of hot water to give, in quantitative yield, a suspension of product that is readily isolated and washed.

All Other Basic Organic Chemical Manufacturing

Benzenamine, 4-nitro-: ACTIVE