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A modern synthesis entails reduction of nitrobenzene to phenylhydroxylamine (C 6 H 5 NHOH) which is then oxidized by sodium dichromate (Na 2 Cr 2 O 7). [5] Nitrosobenzene can also be prepared by oxidation of aniline using peroxymonosulfuric acid (Caro's acid) [6] or potassium peroxymonosulfate under biphasic conditions. [7]
Nitrobenzene is an aromatic nitro compound and the simplest of the nitrobenzenes, with the chemical formula C 6 H 5 NO 2. 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.
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1,3-Dinitrobenzene is accessible by nitration of nitrobenzene. The reaction proceeds under acid catalysis using sulfuric acid. The directing effect of the nitro group of nitrobenzene leads to 93% of the product resulting from nitration at the meta-position. The ortho- and para-products occur in only 6% and 1%, respectively. [1]
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The nitration product produced on the largest scale, by far, is nitrobenzene. Many explosives are produced by nitration including trinitrophenol (picric acid), trinitrotoluene (TNT), and trinitroresorcinol (styphnic acid). [3] Another but more specialized method for making aryl–NO 2 group starts from halogenated phenols, is the Zinke nitration.
Benzidine is prepared in a two step process from nitrobenzene. First, the nitrobenzene is converted to 1,2-diphenylhydrazine , usually using iron powder as the reducing agent. Treatment of this hydrazine with mineral acids induces a rearrangement reaction to 4,4'-benzidine.
Aniline absorbs in the K (220 - 250 nm) and the B (250 - 290 nm) bands exhibited by benzenoid compounds. The K and B bands arise from π to π* transitions as a result of the a group containing multiple bond being attached to the benzene ring. When dissolved in ethanol, λ max for aniline is 230 nm, but in dilute aqueous acid λ max is 203 nm ...