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2-Nitrotoluene is a light yellow to darker yellow-green liquid. It is used for the synthesis of a variety of industrial products. These include to synthesise agricultural and rubber chemicals, azo and sulphur dyes, and dyes for cotton, wool, silk, leather, and paper. O-nitrotoluene decomposes on contact with strong oxidants, reducing agents, acids, or bases producing toxic fumes, nitrogen oxides, and carbon monoxide.
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Clear, colorless to pale yellowish combustible liquid with a faint, aromatic odor. May darken on
exposure to air.
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2-Nitrotoluene is a taggant used in explosive compounds and is often used as a simulant for nitro-based high explosives. Its photodissociation leads to the formation of atomic carbon and its emission is observed to overlap with NO emission. The energy transfer from laser-excited nitrogen to NO leads to a long lifetime of NO emission. Argon atoms stabilise the 2-nitrotoluene molecule and delay its photodissociation.
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ChEBI: 2-nitrotoluene is a mononitrotoluene that is toluene carrying a nitro substituent at position 2. It has a role as an environmental contaminant and a carcinogenic agent.
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2-Nitrotoluene was synthesized by nitration of toluene with mixed acid, A mixture of mononitrotoluene isomers can be prepared from the nitration of toluene between -10 oC and 30 oC. Lower temperatures result in little or no reaction, while higher temperatures will result in double nitration forming dinitrotoluenes.
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Light yellow oily liquid with a characteristic odor of aromatic nitro compounds. Sinks in water. Derived from toluene by nitration and separation by fractional distillation. Flash point 223°F.
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Insoluble in water.
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2-Nitrotoluene is toxic by inhalation, ingestion and skin aborption, targeting the blood, central nervous system, skin, and gastrointestinal tract. Symptoms include, anoxia, weakness or dizziness, nausea and vomiting. If 2-Nitrotoluene contacts the eye, the eye should be irrigated immediately. If 2-Nitrotoluene contacts the skin, the area should be washed with soap. If inhaled, respiratory support should be administered. Finally, if ingested, medical attention should be sought. 2-Nitrotoluene also reacts with sulfuric acid, sodium hydroxide, hydrogen, sodium, tetranitromethane, reducing agents and strong oxidizers. 2-Nitrotoluene is very heat sensitive.
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Toxic by inhalation, ingestion, skin absorption. Methemoglobinemia. Probable carcinogen.
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INHALATION, INGESTION, OR SKIN: Headache, flushing of face, dizziness, dyspnea (difficult breathing), cyanosis, nausea, vomiting, muscular weakness, increased pulse and respiratory rate, irritability, and convulsions. SKIN: Irritation.
Safety Profile
Confirmed carcinogen.
A poison. Moderately toxic by ingestion.
Mucous membrane effects by inhalation.
Mutation data reported. Combustible when
exposed to heat or open flame. To fight fire,
use water spray, fog, foam, CO2. Potentially
explosive reaction with alkali (e.g., sodmm
hydroxide). When heated to decomposition
it emits toxic fumes of NOx. See also other
methylnitrobenzene entries and NITRO
COMPOUNDS OF AROMATIC
HYDROCARBONS.
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The nitrotoluenes are used in the
production of toluidines and other dye intermediates.
All isomers are used in manufacture of agriculture and
rubber chemicals and in various dyes.
Carcinogenicity
o-Nitrotoluene is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals and supporting data on mechanisms of carcinogenesis.
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Biological. Robertson et al. (1992) reported that toluene dioxygenases from Pseudomonas
putida F1 and Pseudomonas sp. Strain JS 150 oxidized the methyl group forming 2-nitrobenzyl
alcohol.
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UN1664 Nitrotoluenes, (o-; m-; p-), Hazard
Class: 6.1; Labels: 6.1-Poisonous materials.
Purification Methods
Crystallise 2-nitrotoluene (repeatedly) from absolute EtOH by cooling in a Dry-ice/alcohol mixture. Further purify it by passing an alcoholic solution through a column of alumina. [Beilstein 5 IV 845.]
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Decomposes on contact with strong oxidizers;
strong acids; reducing agents; strong bases; ammonia,
amines producing toxic fumes, causing fire and explosion
hazard. Heat above 190C may cause explosive decomposition.
Attacks some plastics, rubbers, and coatings.
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Controlled incineration-care
must be taken to maintain complete combustion at all
times. Incineration of large quantities may require scrubbers
to control the emission of nitrogen oxides.
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