Nitrobenzene

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Nitrobenzene

Nitrobenzene, distances in picometers

Nitrobenzene

Names Preferred IUPAC name Other names Identifiers 507540 ChEBI ChEMBL ChemSpider ECHA InfoCard 100.002.469 EC Number 50357 KEGG RTECS number UNII Properties C6H5NO2 Molar mass 123.11 g/mol Appearance yellowish, oily liquid[1] Odor pungent, like paste shoe polish[1] to almond-like Density 1.199 g/cm3 Melting point 5.7 °C (42.3 °F; 278.8 K) Boiling point 210.9 °C (411.6 °F; 484.0 K) 0.19 g/100 ml at 20 °C Vapor pressure 0.3 mmHg (25°C)[1] −61.80·10−6 cm3/mol 1.5215 Viscosity 1.8112 mPa·s[2] Hazards GHS labelling: Danger H301, H311, H331, H351, H360, H372, H412 P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P308+P313, P311, P312, P314, P321, P322, P330, P361, P363, P403+P233, P405, P501 NFPA 704 (fire diamond) Flash point 88 °C (190 °F; 361 K) 480 °C (896 °F; 753 K) Explosive limits 1.8%-?[1] Lethal dose or concentration (LD, LC): 780 mg/kg (rat, oral)600 mg/kg (rat, oral)590 mg/kg (mouse, oral)[3] 750 mg/kg (dog, oral)[3] NIOSH (US health exposure limits): TWA 1 ppm (5 mg/m3) [skin][1] TWA 1 ppm (5 mg/m3) [skin][1] 200 ppm[1] Related compounds AnilineBenzenediazonium chlorideNitrosobenzene

Nitrobenzene is an aromatic nitro compound and the simplest of the nitrobenzenes, with the chemical formula C6H5NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor to aniline. In the laboratory, it is occasionally used as a solvent, especially for electrophilic reagents. As confirmed by X-ray crystallography, nitrobenzene is a planar molecule.[4]

Nitrobenzene is prepared by nitration of benzene with a mixture of concentrated sulfuric acid, water, and nitric acid. This mixture is sometimes called “mixed acid.”

The production of nitrobenzene is one of the most dangerous processes conducted in the chemical industry because of the exothermicity of the reaction (ΔH = −117 kJ/mol).[5]

The nitration process involves formation of the nitronium ion (NO2+), followed by an electrophilic aromatic substitution reaction of it with benzene. The nitronium ion is generated by the reaction of nitric acid and an acidic dehydration agent, typically sulfuric acid:

HNO3 + H+ ⇌ NO2+ + H2O

World capacity for nitrobenzene in 1985 was about 1,700,000 tonnes.[5]

Approximately 95% of nitrobenzene industrially produced is hydrogenated to aniline:[5]

C6H5NO2 + 3 H2 → C6H5NH2 + 2 H2O

Aniline is a precursor to urethane polymers, rubber chemicals, pesticides, dyes (particularly azo dyes), explosives, and pharmaceuticals.

Most aniline is consumed in the production of methylenedianiline, a precursor to polyurethanes.

Nitrobenzene is used to mask unpleasant odors in shoe and floor polishes, leather dressings, paint solvents, and other materials. Redistilled, as oil of mirbane, nitrobenzene had been used as an inexpensive perfume for soaps. It has been replaced by less toxic chemicals for this purpose.[6] A significant merchant market for nitrobenzene is its use in the production of the analgesic paracetamol (also known as acetaminophen).[7] Nitrobenzene is also used in Kerr cells, as it has an unusually large Kerr constant. Evidence suggests its use in agriculture as a plant growth/flowering stimulant.[8]

Aside from its conversion to aniline, nitrobenzene can be selectively reduced to azoxybenzene,[9] azobenzene,[10] nitrosobenzene,[11] hydrazobenzene,[12] and phenylhydroxylamine.[13] It has been used as a mild oxidant in reactions like the Skraup quinoline synthesis.[14]

Nitrobenzene is highly toxic (Threshold Limit Value 5 mg/m3) and readily absorbed through the skin.

Prolonged exposure may cause serious damage to the central nervous system, impair vision, cause liver or kidney damage, anemia and lung irritation. Inhalation of vapors may induce headache, nausea, fatigue, dizziness, cyanosis, weakness in the arms and legs, and in rare cases may be fatal. The oil is readily absorbed through the skin and may increase heart rate, cause convulsions or rarely death. Ingestion may similarly cause headaches, dizziness, nausea, vomiting and gastrointestinal irritation, loss of sensation/use in limbs and also causes internal bleeding.[11]

Nitrobenzene is considered a likely human carcinogen by the United States Environmental Protection Agency,[15] and is classified by the IARC as a Group 2B carcinogen which is “possibly carcinogenic to humans”.[16] It has been shown to cause liver, kidney, and thyroid adenomas and carcinomas in rats.[17]

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.[18]