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Home > Encyclopedia > 3-Nitroaniline

3-Nitroaniline

3-Nitroaniline structure

3-Nitroaniline 

structure
  • CAS No:

    99-09-2

  • Formula:

    C6H6N2O2

  • Chemical Name:

    3-Nitroaniline

  • Synonyms:

    Benzenamine,3-nitro-;Aniline,m-nitro-;3-Nitrobenzenamine;C.I. 37030;Amarthol Fast Orange R Base;Azobase MNA;Daito Orange Base R;Devol Orange R;Diazo Fast Orange R;Fast Orange M Base;Fast Orange R Base;Fast Orange MM Base;Hiltonil Fast Orange R Base;Fast Orange Base R;MNA;Naphtoelan Orange R Base;m-Nitroaniline;Orange Base Irga I;3-Nitroaniline;C.I. Azoic Diazo Component 7;Fast Orange R Salt;m-Nitrophenylamine;Nitranilin;1-Amino-3-nitrobenzene;m-Aminonitrobenzene;m-Nitroaminobenzene;meta-Nitroaniline;3-Aminonitrobenzene;3-Nitrophenylamine;NSC 9574;m-Aminonitrobenze;12262-63-4

  • Categories:

    Organic Chemistry  >  Amides

Description

​3-Nitroaniline, also known as m-nitroaniline, is an organic compound with the formula C₆H₆N₂O₂. It appears as a yellow crystalline solid with a melting point of 114 °C and a boiling point of 306 °C. The compound is slightly soluble in water but readily dissolves in organic solvents such as ethanol, ether, and chloroform. ​

3-Nitroaniline Basic Attributes

138.12

138.12

636962

202-729-1

CM50SM561T

0307

9574

1661

DTXSID6025725

Yellow crystals from water|YELLOW RHOMBIC NEEDLES

29214210

Characteristics

71.8

1.37

Yellow to ochre-yellow to orange Crystals, Crystalline Powder and/or Chunks

0.9011 g/cm3 @ Temp: 25 °C

114 °C

306 °C

196 °C

1.634

H2O: 1.25 g/L

Store below +30°C.

1 mm Hg ( 119 °C)

Oral-rat LD50: 535 mg/kg;Oral-Mouse LD50: 308 mg/kg

Combustible in case of open flame; burning produces toxic nitrogen oxide fumes; reacts with oxidant

Burning sweet odor

7.91e-09 atm-m3/mole|Henry's Law constant = 7.91X10-9 atm-cu m/mol at 25 °C

pKa = 2.466 at 25 °C

Forms water-soluble salts with mineral acids|Hydroxyl radical reaction rate constant = 9.41X10-12 cu cm/molec-sec at 25 °C (est)

Insoluble in water.

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

Thermal stability of this compound is reduced by various impurities. This compound may be sensitive to prolonged exposure to light. This compound may react explosively with ethylene oxide at 266° F. It is incompatible with acids (nitric, sulfuric), acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents. (NTP, 1992). Unstable when heated.

Dust explosion possible if in powder or granular form, mixed with air.

108 kJ/mol

Safety Information

II

6.1

UN 1661 6.1/PG 2

2

23/24/25-33-52/53

28-36/37-45-61-28A

BY6825000

T

The warehouse is ventilated at low temperature and dry; stored separately from oxidants, acids and food additives

Stable at room temperature in closed containers under normal storage and handling conditions.

P261-P273-P280-P301 + P310-P311

H301-H311-H331-H373-H412

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.

Possibly explosive reaction with ethylene oxide at 130 °C.|FORMS WATER-SOL SALTS WITH MINERAL ACIDS.

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.

UN 1661

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)|Combustible. Many reactions may cause fire or explosion. Finely dispersed particles form explosive mixtures in air.

|Danger|H301+H311+H331 (97.58%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]|P260, P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P311, P312, P314, P321, P322, P330, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 454 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P264, P270, P273, P281, P301+P312, P307+P311, P308+P313, P314, P321, P330, P391, P405, and P501|Warning|P201, P202, P260, P264, P270, P281, P301+P312, P308+P313, P309+P311, P314, P330, P405, 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, 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. STORAGE PRECAUTIONS: You should keep this material in a tightly-closed container under an inert atmosphere, and store it at refrigerated temperatures. You should protect this compound from exposure to light. STORE AWAY FROM SOURCES OF IGNITION. (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)|Wear butyl rubber gloves, protective working clothes, self-contained breathing apparatus, protective shoes.|Employees should be provided with and required to use impervious clothing, gloves, face-shields (eight-inch minimum), and other appropriate protective clothing necessary to prevent any possibility of skin contact with solid 4-nitroaniline or liquids containing 4-nitroaniline. Employees should be provided with and required to use dust and splash-proof safety goggles where there is any possibility of liquid 4-nitroaniline or solids containing 4-nitroaniline contacting the eyes. /4-Niroaniline/|The following types of respirators should be selected under the prescribed concentrations: 30 mg/cu m: 1) Any supplied-air respirator 2) Any self-contained breathing apparatus. 75 mg/cu m: Any supplied-air respirator operated in a continuous flow mode. 150 mg/cu m: 1) Any self-contained breathing apparatus with full facepiece 2) Any supplied-air respirator with a full facepiece. 300 mg/cu m: Any supplied-air respirator with a half-mask and operated in a pressure-demand or other positive pressure mode. Emergency or planned entry in unknown concentration or immediately dangerous to life or health (IDLH) conditions: 1) Any self-contained breathing apparatus with full facepiece and operated in a pressure-demand or other positive pressure mode 2)Any supplied-air respirator with a full face piece and operated in pressure-demand or other positive pressure mode in combination with an auxiliary self-contained breathing apparatus operated in pressure-demand or other positive pressure mode.

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

PREVENT DISPERSION OF DUST! Do not eat, drink, or smoke during work. Wash hands before eating.|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.|AVOID BREATHING DUST; AVOID CONTACT WITH SKIN, EYES, CLOTHING.|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.|For more Preventive Measures (Complete) data for 3-NITROANILINE (7 total), please visit the HSDB record page.

/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. /Nitroanilines/|/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. /Nitroanilines/|/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. /Nitroanilines/|/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. /Nitroanilines/|For more DOT Emergency Guidelines (Complete) data for 3-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.

Dust: irritating to eyes, nose and throat; solid: irritating to skin & eyes

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.

Separated from strong acids, strong oxidants, combustible substances, reducing agents and food and feedstuffs. Dry.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance may cause effects on the blood. This may result in the formation of methaemoglobin. Medical observation is indicated. The effects may be delayed.

The substance may have effects on the blood. This may result in the formation of methaemoglobin.

NO open flames. NO contact with combustible substances. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.

PREVENT DISPERSION OF DUST!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

Raw wastewater collected from a US dye manufacturing plant on the Black River in July 1976 contained 270 ppb nitroaniline (isomers unspecified); the final treated effluent contained no detectable levels of nitroaniline(1).

Toxicity

highly toxic

LD50 Rat oral, SD strain (M), 540 mg/kg|LD50 RAT ORAL 900 MG/KG.|LD50 Mouse oral, CF-1 (M), 310 mg/kg|LD50 Mouse oral 308 mg/kg|For more Non-Human Toxicity Values (Complete) data for 3-NITROANILINE (6 total), please visit the HSDB record page.

/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. ...

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.

3-Nitroaniline's production and use as an intermediate in the synthesis of dyes and pigments(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 44(2) and 87(3), indicate that 3-nitroaniline is expected to have very high to 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 3-nitroaniline from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 7.9X10-9 atm-cu m/mole(4). 3-Nitroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.56X10-5 mm Hg(5). 3-Nitroaniline was determined to be non-biodegradable using the Japanese MITI protocol(6), indicating that biodegradation is not an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), Koc values of 44(2) and 87(3) indicate that 3-nitroaniline is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon a Henry's Law constant of 7.9X10-9 atm-cu m/mole(5). According to a classification scheme(6), BCFs of <10(7,8), suggest bioconcentration in aquatic organisms is low(SRC). 3-Nitroaniline is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 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 alkoxy radicals(9); reactions with 3-nitroaniline are likely to be somewhat slower due to the presence of the nitro function(SRC). 3-Nitroaniline was determined to be non-biodegradable using the Japanese MITI protocol(8), 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), 3-nitroaniline, which has a vapor pressure of 9.56X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 3-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 41 hours(SRC), calculated from its rate constant of 9.4X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 3-nitroaniline may be removed from the air by wet or dry deposition(SRC). 3-Nitroaniline does absorb light 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 3-nitroaniline with photochemically-produced hydroxyl radicals has been estimated as 9.4X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 41 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 3-Nitroaniline is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Aromatic amines react relatively rapidly in natural water with photochemically produced oxidants such as hydroxyl radicals and alkoxy radicals(3); half-lives of aniline are on the order of 30 hr of sunlight for hydroxyl radicals and 19 hr of sunlight for peroxy radicals(3); reactions with 3-nitroaniline are likely to be somewhat slower due to the presence of the nitro function(SRC). 3-Nitroaniline does absorb light at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

3.02|A 6-week bioconcentration study in carp obtained BCF values of 1.1-3.0 and <10 for concentrations of 3- nitroaniline of 0.5 and 0.05 mg/L, respectively(1). An aquarium study using carp fish found 3-nitroaniline to have a low bioaccumulation potential(2). A study using zebrafish experimentally determined the BCF for 3-nitroaniline to be 8.3(3). According to a classification scheme(4), these BCF values suggest bioconcentration in aquatic organisms is low(SRC).

53.70 L/kg|Soil adsorption studies using four silt loam soils and a 2-hour adsorption period determined a mean log Kom of 1.70 which corresponds to a Koc of 87 for 3-nitroaniline(1). 3-Nitroaniline had a measured log Koc of 1.64 which corresponds to a Koc value of 44(2). According to a classification scheme(3), these Koc values suggest that 3-nitroaniline is expected to have very high to high mobility in soil(SRC). 3-Nitroaniline was found to have a Kd value of 3.5 L/kg in homoionic K+ Montmorillonite type soil(4). However, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(5,6), suggesting that mobility may be much lower in some soils(SRC).

The Henry's Law constant for 3-nitroaniline is 7.9X10-9 atm-cu m/mole(1). This Henry's Law constant indicates that 3-nitroaniline is expected to be essentially nonvolatile from water surfaces(2). 3-Nitroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.56X10-5 mm Hg(3).

GROUNDWATER: For samples collected from 1981 to 1986, 3-nitroaniline was not detected in hazardous waste site groundwater samples in EPA regions 1-3, 5-6, and 8-10, and was not analyzed in regions 4 and 7(1).|SURFACE WATER: A concentration of 0.1 ppb 3-nitroaniline was identified in water taken from the Rhine River near Labith, Netherlands(1).

Occupational exposure to 3-nitroaniline may occur through dermal contact with this compound at workplaces where 3-nitroaniline is produced or used. (SRC)

Drug Information

IT IS READILY ABSORBED THROUGH INTACT SKIN ... .

M-NITROANILINE YIELDS 2-AMINO-4-NITROPHENOL, M-PHENYLENEDIAMINE, & 4-AMINO-2-NITROPHENOL IN RABBIT; YIELDS M-NITROANILINE-N-GLUCOSIDE IN BEAN. /FROM TABLE/|... A simplified version of the isolated vascularly perfused rat small intestine was developed ... with 1,3-dinitrobenzene (1,3-DNB) as a model xenobiotic. Both 3-nitroaniline (3-NA) and 3-nitroacetanilide (3-NAA) were formed and absorbed following intralumenal doses of 1,3-DNB (1.8 or 4.2 umol) to isolated vascularly perfused rat small intestine. Dose, fasting, or antibiotic pretreatment had no effect on the absorption and metabolism of 1,3-DNB in this model system. The failure of antibiotic pretreatment to alter the metabolism of 1,3-DNA indicated that 1,3-DNB metabolism was mammalian rather than microfloral in origin. ...|... 1,3-Dinitrobenzene (1,3-DNB), which is known to undergo reductive biotransformation in an intact, oxygenated isolated perfused intestinal preparation, was used as a model substrate for reductive enzymes of the small intestine of the rat. Subcellular fractions from duodenal, jejunal, and ileal regions of rat small intestinal mucosa were used to characterize the enzyme source(s) of those reductive reactions of 1,3-DNB that are relevant in the oxygenated intestinal tissue. 1,3-DNB was reduced to 3-nitroaniline (3-NA) by cytosol from duodenum and jejunum. The rate of reduction was 2 times faster when incubations contained duodenal rather than jejunal cytosol. Jejunal cytosol-catalyzed reduction of 1,3-DNB was supported by hypoxanthine, NADPH, or NADH. Duodenal microsomes catalyzed the reduction of 1,3-DNB to 3-NA in the presence of supplemental NADPH or NADH; however, the reaction was very slow. Jejunal microsomes, ileal microsomes, and ileal cytosol failed to catalyze the reduction of 1,3-DNB. Studies with chemical inhibitors suggested possible roles for DT diaphorase, glutathione reductase, or xanthine oxidase in the jejunal cytosol-catalyzed reaction. Purified, commercially available xanthine oxidase (from buttermilk) catalyzed the reduction of 1,3-DNB to 3-NA when supplemented with NADH or hypoxanthine.|The metabolism of 1,3-dinitrobenzene by rat testicular subcellular fractions (microsomes, cytosol or 9000 x g supernatant (S-9)) was studied. The effects of NADPH, oxygen, glutathione (GSH) and carbon monoxide upon the rate of metabolism were determined. Three metabolites were identified, and characterised as 3-nitrosonitrobenzene, 3-nitrophenylhydroxylamine and 3-nitroaniline by co-chromatography with authentic standards. ...|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.

0.17 Days

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.

SYMPTOMS: Symptoms of exposure to this compound may include cyanosis and liver damage. When inhaled or ingested, this compound may cause headache, flushing of the face, difficult breathing, nausea, vomiting, weakness, drowsiness, irritability and dermatitis. Structurally similar chemicals may cause methemoglobinemia. ACUTE/CHRONIC HAZARDS: This chemical is a highly toxic irritant. It may be fatal if inhaled or swallowed. It causes eye and skin irritation. When heated to decomposition this compound emits toxic fumes of carbon monoxide, carbon dioxide and oxides of nitrogen. (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)


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.

INHALATION: Fresh air, rest. Artificial respiration if indicated. Refer for medical attention. SKIN: Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention. EYES: First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then take to a doctor.|/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aniline and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aniline and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. DIRECT PHYSICIAN ORDER ONLY ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aniline and related compounds/

/SIGNS AND SYMPTOMS/ Acute exposure can cause methemoglobinemia, cyanosis. Chronic exposure may cause liver damage|/SIGNS AND SYMPTOMS/ Symptomatology: 1. Lips, tongue, and mucous membranes navy blue to black; skin slate gray, all without signs of cardiac or pulmonary insufficiency. 2. Severe headache, nausea, sometimes vomiting, dryness of throat. 3. Central nervous symptoms: confusion, ataxia, vertigo, tinnitus, weakness, disorientation, lethargy, drowsiness, and finally, coma. Convulsions may occur but appear to be uncommon. 4. Cardiac effects: heart blocks, arrhythmias, and shock. 5. Death, although uncommon, is usually due to cardiovascular collapse and not resp paralysis. 6. Urinary signs and symptoms may incl painful micturition, hematuria, hemoglobinuria, and renal insufficiency (usually mild). 7. A late acute hemolytic episode should be anticipated at 6 to 8 days after ingestion. /Aniline/|/OTHER TOXICITY INFORMATION/ ... Powerful methemoglobin former with attendant hemolytic effect..|/OTHER TOXICITY INFORMATION/ On prolonged and excessive exposures it may ... cause liver damage. ... Its vapors are highly toxic as well.

3-NA, aniline

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

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


MAY BE ABSORBED! Further see Inhalation.

3-Nitroaniline Use and Manufacturing

Methods of Manufacturing

Using nitrobenzene as a raw material, nitric acid and sulfuric acid are mixed to form a mixed acid for nitrification to produce m-dinitrobenzene, which is refined by sulfurous acid to obtain a finished product of m-dinitrobenzene. Sulfur and sodium sulfide are used as raw materials to prepare sodium polysulfide, and sodium polysulfide is used to reduce m-dinitrobenzene to m-nitroaniline. The reaction product is recrystallized and filtered to obtain a finished product. Raw material consumption quota: nitrobenzene 1319kg/t, nitric acid 845kg/t, sulfuric acid 2050kg/t, sodium sulfide 707kg/t, sulfur 271kg/t.

Uses

3-nitroaniline serves primarily as an intermediate in the synthesis of azo dyes. It is used in the production of dyes like Disperse Yellow 5 and Acid Blue 29.

Production

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1976) 2.27X10+6 GRAMS (EST)|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4052]

Benzenamine, 3-nitro-: ACTIVE

28 AROMATIC AND ALIPHATIC AMINES WERE SEPARATED BY TLC USING SILICA GEL PLATES; 20 SOLVENT SYSTEMS WERE EXAMINED.|APPLICATIONS OF FUSED SILICA CAPILLARY COLUMNS (FSCC)/MS (MASS SPECTROMETRY) TO ANALYSIS OF 28 CMPD INCLUDING A NUMBER OF CHLORO- AND NITRO-SUBSTITUTED ANILINES IN ENVIRONMENTAL SAMPLES ARE PRESENTED. SAMPLES INCL VENT EMISSIONS FROM A FUNGICIDE MANUFACTURING PROCESS AND CONTAMINATED SOIL AND WATER SAMPLES.|TWO COMPLEMENTARY METHODS FOR ANALYSIS OF PRIMARY AROMATIC AMINES IN A MIXT SUCH AS AIR WERE REPORTED: A TLC METHOD FOR RAPID SCREENING WITH A LOW-NANOGRAM DETECTION LEVEL, AND A HIGH-PERFORMANCE LIQUID CHROMATOGRAPHIC (HPLC) METHOD WITH A PICOGRAM DETECTION CAPABILITY.|Analyte: Aromatic Amines; Matrix: air; Procedure: adsorption on silica gel; elution by ethanol; Gas Chromatography analysis; Range: 0.01-14 mg/sample.|For more Analytic Laboratory Methods (Complete) data for 3-NITROANILINE (13 total), please visit the HSDB record page.

Analysis Methods

Name Column Shape Active Phase(℃) Retention index Temperature Control Method Comments Reference
Kovats' RI, non-polar column, isothermal Packed SE-30 1446. 180. isothermal N2, Chromosorb A AW; Column length: 3. m Oszczapowicz, J.Osek, J.Ciszkowski, K.Krawczyk, W.Ostrowski, M.Retention Indices of Dimethylbenzamidines and Benzylideneamines on a Non-Polar ColumnJ. Chromatogr.1985, 330, 79-85.
Kovats' RI, non-polar column, isothermal Packed SE-30 1446. 180. isothermal N2, Chromosorb W AW; Column length: 3. m Oszczapowicz, J.Osek, J.Dolecka, E.Retention indices of dimethylformamidines, dimethylacetamidines and tetramethylguanidines on a non-polar columnJ. Chromatogr.1984, 315, 95-100.
Kovats' RI, non-polar column, isothermal Capillary DB-5 254.2 temperature ramp 30. m/0.32 mm/0.25 μm, He, 40. C @ 3. min, 8. K/min, 285. C @ 29.5 min Donnelly, J.R.Abdel-Hamid, M.S.Jeter, J.L.Gurka, D.F.Application of gas chromatographic retention properties to the identification of environmental contaminantsJ. Chromatogr.1993, 642, 1-2, 409-415.
Kovats' RI, non-polar column, isothermal Capillary Polydimethyl siloxanes 254.17 custom temperature program Program: not specified Eckel, W.P.Kind, T.Use of boiling point-Lee retention index correlation for rapid review of gas chromatography-mass spectrometry dataAnal. Chim. Acta.2003, 494, 1-2, 235-243.

Computed Properties

Molecular Weight:138.12
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:138.042927438
Monoisotopic Mass:138.042927438
Topological Polar Surface Area:71.8
Heavy Atom Count:10
Complexity:132
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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