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The reduction of nitro compounds are chemical reactions of wide interest in organic chemistry. The conversion can be effected by many reagents. The nitro group was one of the first functional groups to be reduced. Alkyl and aryl nitro compounds behave differently. Most useful is the reduction of aryl nitro compounds.
with the formula HOC 6 H 4 NO 2.Three isomeric nitrophenols exist: . o-Nitrophenol (2-nitrophenol; OH and NO 2 groups are neighboring, a yellow solid.; m-Nitrophenol (3-nitrophenol, CAS number: 554-84-7), a yellow solid (m.p. 97 °C) and precursor to the drug mesalazine (5-aminosalicylic acid).
ArN(O)=NAr' + C 6 H 12 O 6 → ArN=NAr' + C 6 H 10 O 6 + H 2 O. For textile dying, a typical nitro coupling partner would be disodium 4,4′-dinitrostilbene-2,2′-disulfonate. Typical aniline partners are shown below. [6] An orange azo dye Solvent Yellow 7. As a consequence of π-delocalization, aryl azo compounds have vivid colors
The structure of an organic nitro compound. In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups (−NO 2). The nitro group is one of the most common explosophores (functional group that makes a compound explosive) used globally. The nitro group is also strongly electron-withdrawing.
4-Nitrophenol is a product of the enzymatic cleavage of several synthetic substrates such as 4-nitrophenyl phosphate (used as a substrate for alkaline phosphatase), 4-nitrophenyl acetate (for carbonic anhydrase), 4-nitrophenyl-β-D-glucopyranoside and other sugar derivatives which are used to assay various glycosidase enzymes.
Illustrative is the reaction of phenol with benzenediazonium chloride to give a Solvent Yellow 7, a yellow-orange azo compound. The reaction is faster at high pH. [2] Many other azo dyes have been prepared by similarly. Several procedures have been described in detail. [5] [6] [7] Naphthols are popular coupling agents.
Azobenzene is a weak base, but undergoes protonation at one nitrogen with a pK a = -2.95. It functions as a Lewis base, e.g. toward boron trihalides. It binds to low valence metal centers, e.g. Ni(Ph 2 N 2)(PPh 3) 2 is well characterized. [14] Azobenzene oxidizes to give azoxybenzene. Hydrogenation gives diphenylhydrazine.
Azoxybenzene and its derivatives are typically prepared by reduction of nitrocompounds, such as the reduction of nitrobenzene with arsenous oxide. [2] Such reactions are proposed to proceed via the intermediacy of the nitroso compounds and hydroxylamines, e.g. phenylhydroxylamine and nitrosobenzene (Ph = phenyl, C 6 H 5): [3]: 445 + +