nitrobenzene


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nitrobenzene,

C6H5NO2, very poisonous, flammable, pale yellow, liquid aromatic compound with an odor like that of bitter almonds. It is sometimes called oil of mirbane or nitrobenzol. Nitrobenzene melts at 5.85°C;, boils at 210.9°C;, is only slightly soluble in water, but is very soluble in ethanol, ether, and benzene. It is prepared by treating benzene with a mixture of nitric and sulfuric acids; in the resulting nitration reaction, one hydrogen in the benzene molecule is replaced with a nitro group, NO2. The major use of nitrobenzene is in the production of anilineaniline
, C6H5NH2, colorless, oily, basic liquid organic compound; chemically, a primary aromatic amine whose molecule is formed by replacing one hydrogen atom of a benzene molecule with an amino group.
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, commercially the most important amine; nitrobenzene is heated with iron and dilute hydrochloric acid, and the resulting anilinium chloride is treated with sodium carbonate to release aniline. In the pharmaceutical industry nitrobenzene is used in the production of the analgesic acetaminophenacetaminophen
, an analgesic and fever-reducing medicine. It is an active ingredient in many over-the-counter medicines, including Tylenol and Midol. Introduced in the early 1900s, acetaminophen is a coal tar derivative that acts by interfering with the synthesis of
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, or paracetamol. Nitrobenzene is also used in shoe and floor polishes, leather dressings, and paint solvents to mask unpleasant odors. As oil of mirbane, nitrobenzene was used as an inexpensive perfume for soaps and cosmetics but is now considered too toxic for such applications.

Nitrobenzene

 

C6H5NO2, the simplest aromatic nitro compound; an oily light yellow liquid. Melting point, 5.7°C; boiling point, 210.9°C; density, 1.987 g/cm3 at 25°C. It is poorly soluble in water but mixes well with organic solvents.

Upon reduction, nitrobenzene is converted to aniline or hydrazobenzene, depending on the conditions. Under the action of acids, hydrazobenzene isomerizes to benzidine. Nitration, sulfonation, and chlorination of nitrobenzene take place mainly at the meta- position to the nitro group, for example:

Nitrobenzene is produced by nitration of benzene by a nitrating mixture. It is poisonous, with a maximum permissible concentration in air of 3 mg/m3 in work areas and 0.008 mg/m3 in residential buildings.

Nitrobenzene is mainly used in the production of aniline. In small quantities, nitrobenzene is also used in the production of intermediates for dyes (methanilic acid and benzidine), and also certain dyes (for example, induline).

REFERENCE

Orlova, E. Iu. Khimiia i tekhnologiia brizantnykh vzryvchatykh ve-shchestv. Leningrad, 1973.

nitrobenzene

[¦nī·trō′ben‚zēn]
(organic chemistry)
C6H5NO2 Greenish crystals or a yellowish liquid, melting point 5.70°C; a toxic material; used in aniline manufacture. Also known as oil of mirbane.
References in periodicals archive ?
Case of acute methemoglobinemia caused by nitrobenzene ingestion.
Moreover, the study also identifies that Flow velocity in the river is most sensitive parameter to Nitrobenzene concentration in water column based on sensitivity analysis of input parameters and the organic pollutants were the main contributing factor to the toxicity of effluents from textile and dyeing plants, pulp and paper mills, fine chemical factories and municipal wastewater treatment plants.
Nitrobenzene is an oxidising compound used in the manufacture of aniline, pesticides, rubber chemicals and printing materials.
Different spectrophotometric procedures have been reported for determination of PEH including the formation of ion-pair complexes between the drug and alizarine, alizarine red S, alizarine yellow G or quinalizarine [14], ninhydrin in sulfuric acid [15], nitrobenzene derivates in acetonitrile medium [16], oxidative coupling with 4-aminoantipyrine in the presence of potassium ferricyanide or sodium periodate [17,18], diazotized p-nitroaniline or 2-aminobenzothiazol in alkaline medium [19,20], forming a charge transfer complex with chloranil or haematoxylin in alkaline medium [21,22]= 7and[23].
Common causes of acquired methaemoglobinaemia Acetanilid Naphthoquinone p-amino salicylic acid Naphthalene Aniline dyes Nitrites Benzene derivatives Nitroglycerin Clofazimine Nitric oxide Chlorates Nitrobenzene Chloroquine Paraquat Dapsone Phenacetin Local anaesthetic agents Phenazopyridine Metoclopramide Primaquine Methylene blue (paradoxically can transiently Sulfonamides worsen methaemoglobinaemia)
He then worked for ICI, on Leeds Road, where it is thought he was exposed to nitrobenzene, which can cause cancer.
RATIO (%) Ethanol 39 100 Slight turbid IPA 20 76 Slight milky, clear Acetone 20 42 Milky solution, 1 big lump remaining Butyl acetate 60 63 Milky PM 30 100 Dissolved DPM 30 90 Clear solution, 2 small lumps remaining TPM 60 70 Dusty solution MEK 20 100 Dissolved DBE 60 19 Milky DMF 30 100 Dissolved THF 60 67 Clear NMP 40 100 Dissolved Toluene Not dissolved 0 Turbid Isopar G 60 7 Milky Acetonitrile 60 2 Milky Nitrobenzene 60 1 Yellowish TABLE 3.
The team found that if then they added trace amounts of nitrobenzene - a member of the same chemical family as many explosives - they could reverse the effect of oligomycin and switch the mitochondria back on.
A reaction of nitrobenzene hydrogenation to aniline is considered (Gabrielsson et al.