2-Nitroaniline
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2-Nitroaniline
structure -
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CAS No:
88-74-4
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Formula:
C6H6N2O2
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Chemical Name:
2-Nitroaniline
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Synonyms:
Benzenamine,2-nitro-;Aniline,o-nitro-;2-Nitrobenzenamine;Azoene Fast Orange GR Base;Azoene Fast Orange GR Salt;Azofix Orange GR Salt;Azogene Fast Orange GR;Brentamine Fast Orange GR Base;Brentamine Fast Orange GR Salt;Devol Orange B;Devol Orange Salt B;Fast Orange O Base;Fast Orange Base JR;Fast Orange GR Base;Fast Orange O Salt;Fast Orange Salt JR;Hiltonil Fast Orange GR Base;Hiltosal Fast Orange GR Salt;Hindasol Orange GR Salt;Natasol Fast Orange GR Salt;o-Nitroaniline;ONA;Orange Base Ciba II;Orange Base Irga II;Orange GRS Salt;Orange Salt Ciba II;Orange Salt Irga II;2-Nitroaniline;1-Amino-2-nitrobenzene;o-Nitrophenylamine;2-Nitrophenylamine;2-Aminonitrobenzene;o-Aminonitrobenzene;1-Nitro-2-aminobenzene;o-Nitrobenzenamine;NSC 9796
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CAS No:
Description
orange solid
O-nitroaniline is an orange solid with a musty odor. Sinks and mixes slowly with water. (USCG, 1999)|ORANGE-YELLOW CRYSTALS.
O-nitroaniline is an orange solid with a musty odor. Sinks and mixes slowly with water. (USCG, 1999)
2-Nitroaniline Basic Attributes
138.12
138.12
509275
201-855-4
2519U0541L
0306
9796
1661
DTXSID1025726
Yellow-orange crystals from boiling water|Orange-red needles
29214210
Characteristics
71.8
1.44
Orange to brown Crystals or Flakes
0.9015 g/cm3 @ Temp: 25 °C
69-71 °C
284 °C
168 °C
1.5362 (100ºC)
H2O: 1.1 g/L (20 ºC);methanol: 0.1 g/mL, clear
2-8°C
Vapour pressure, Pa at 20°C: 4
4.77 (NTP, 1992) (Relative to Air)
Oral-rat LD50: 1600 mg/kg; Oral-Mouse LD50: 1070 mg/kg
Open flame is flammable; burning produces toxic nitrogen oxide fumes
Musty
5.90e-08 atm-m3/mole|Henry's Law constant = 5.90X10-8 atm-cu m/mol at 25 °C
pKa = -0.28
Ideal Gas Heat of Formation = 6.38X10+7 Joules/kmol|Liquid molar volume is 0.1358 cu m/kmol|Forms water soluble salts with mineral acids|Hydroxyl radical reaction rate constant = 1.35X10-11 cu cm/molec-sec at 25 °C (est)
Insoluble in water.
Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
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)
970 °F (USCG, 1999)|970 °F; 521 °C|521 °C
-10,000 Btu/lb= -5,550 cal/g= -232x10+5 J/kg
Dust explosion possible if in powder or granular form, mixed with air.
Safety Information
II
6.1
UN 1661 6.1/PG 2
2
23/24/25-33-52/53-39/23/24/25-11
28-36/37-45-61-28A-16-7
BY6650000
T,F
The warehouse is ventilated at low temperature and dry; stored separately from oxidants, acids and food additives
Stable. Incompatible with acids, acid chlorides, acid anhydrides, strong oxidizing agents, chloroformates, hexanitroethane.
P260, P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P311, P312, P314, P321, P322, P330, P361, P363, P403+P233, P405, P501
H301
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.
Forms extremely explosive addition compounds with hexanitroethane. Vigorous reaction with sulfuric acid above 200 °C.|FORMS WATER-SOL SALTS WITH MINERAL ACIDS.
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.
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.
|Danger|H301 (97.61%): Toxic if swallowed [Danger Acute toxicity, oral]|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 210 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P281, P301+P312, P305+P351+P338, P308+P313, P330, P337+P313, 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 chemical from exposure to light. (NTP, 1992)
Self-contained breathing apparatus; neoprene gauntlets; safety goggles; rubber or neoprene sealed-tongue work shoes and apron; close-weave cotton coveralls capable of closing at wrist and ankle (USCG, 1999)|Neoprene gauntlets; rubber or neoprene sealed-tongue work shoes and apron; close-weave cotton coveralls capable of closing at wrist and ankle.|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-Nitroaniline/|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.
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/
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.
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.
/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 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.
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.
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. The effects may be delayed. Medical observation is indicated.
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.
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.
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).
Toxicity
moderately toxic
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.
LD50 Rat oral, Sprague Dawley (M & F), 2050 mg/kg|LD50 Rabbit dermal, New Zealand white (female), 20,000 mg/kg bw|LD50 Mouse oral 1290 mg/kg bw|LD50 Rat oral, Wistar (female), 1838 mg/kg bw|For more Non-Human Toxicity Values (Complete) data for 2-NITROANILINE (8 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.
2-Nitroaniline's production and use as an intermediate in the synthesis of dyes and pigments(1,2) may result in its release to the environment through various waste streams(SRC).
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).
The rate constant for the vapor-phase reaction of 2-nitroaniline with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 29 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2-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 alkoxy radicals(3); reactions with 2-nitroaniline are likely to be somewhat slower due to the presence of the nitro function(SRC). 2-Nitroaniline does absorb light at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).
10.00|A 6 week bioconcentration study obtained BCF values of 2.1-4.9 and <10 for concentrations of 2- nitroaniline of 0.5 and 0.05 mg/L, respectively(1). An aquarium study using carp fish found 2-nitroaniline to have a low bioaccumulation potential(2). A study using zebrafish experimentally determined the BCF for 2-nitroaniline to be 8.1(3). According to a classification scheme(4), these BCF values suggest bioconcentration in aquatic organisms is low(SRC).
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).
The Henry's Law constant for 2-nitroaniline is 5.9X10-8 atm-cu m/mole(1). This Henry's Law constant indicates that 2-nitroaniline is expected to be essentially nonvolatile from water surfaces(2). 2-Nitroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.77X10-3 mm Hg(3).
GROUNDWATER: For samples collected from 1981 to 1986, 2-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: 2-Nitroaniline was qualitatively detected in the River Waal at Brakel in the Netherlands during monitoring conducted between 1972-1974(1). A 2-nitroaniline concn of 1 ppb was found in the Rhine River at Lobith, Netherlands in July 1979(2).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 1612 workers (455 of these are female) are potentially exposed to 2-nitroaniline in the US(1). Occupational exposure to 2-nitroaniline may occur through dermal contact with this compound at workplaces where 2-nitroaniline is produced or used(SRC).
Drug Information
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.
0.35 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. /AMINOANILINES/
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)
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. ... . 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. /M-NITROANILINE/|/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/ Toxicity: Moderately toxic by ingestion. Mildly toxic by skin contact.|/OTHER TOXICITY INFORMATION/ ... TOXICITY IS PRACTICALLY IDENTICAL WITH ... THE META AND PARA ISOMERS.
2-nitroaniline
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.
2-Nitroaniline Use and Manufacturing
The preparation method is obtained by ammonolysis of o-chloronitrobenzene. The process is carried out continuously in a high-pressure pipeline reactor at a pressure of 14.7 MPa and a temperature of 230°C. When o-chloronitrobenzene and ammonia enter the reaction pipeline, they stay for 20 minutes The pressure is reduced to 98kPa by the pneumatic membrane regulating valve once, and then enters the expansion tank for evaporation and deamination. The evaporated ammonia enters the ammonia absorption pipe through the jet pump for circulation and absorption. After adding part of the liquid ammonia, it is continued to be used for ammonia desorption and removal. The material of ammonia can be obtained after post-processing.
Dyestuff intermediate.
(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#2867]|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).
ESSENTIALLY 100% FOR DYE MANUFACTURE (1972)
Grades or Purity: Commercial, 100%
Benzenamine, 2-nitro-: ACTIVE
Determination of p- and o-nitroanilines in wastewater by two-wavelength spectrophotometric method was discussed.|A detailed evaluation of gas chromatography and high performance liquid chromatography methods for the determination of anilines in aquatic media was conducted. An optimized analytical approach based on chromatography with thermionic N-P selective detection was described. This method determined a variety of anilines at the low ppb level in industrial aq discharges, and effluents from publicly owned treatment works. Method performance data for authentic environmental samples were presented. Analytical precision was generally 5-15% RSD (relative standard deviation) and recoveries were generally 75%. /Anilines and substituted derivatives/|Analyte: aromatic amines; Matrix: air; Procedure: adsorption on silica gel; elution by ethanol; Gas Chromatography analysis; Range: 0.01-14 mg/sample; Precision: + or - 9%.|THIN LAYER CHROMATOGRAPHY USED TO DETERMINE ANILINES USING FLUORESCAMINE REAGENT.|For more Analytic Laboratory Methods (Complete) data for 2-NITROANILINE (11 total), please visit the HSDB record page.
Computed Properties
Molecular Weight:138.12
XLogP3:1.9
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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