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Another use of 4-nitrochlorobenzene is its condensation with aniline to produce 4-nitrodiphenylamine. Reductive alkylation of the nitro group affords secondary aryl amines, which are useful antioxidants for rubber. 4-Nitrochlorobenzene is the precursor to the anti-leprosy drug Dapsone (4-[(4-aminobenzene)sulfonyl]aniline). [2]
Unlike the other isomers of nitrochlorobenzene, the meta isomer is not activated to nucleophilic substitution at the chlorine center. [1] However, 3-nitrochlorobenzene has other interesting reactivity. 3-Nitrochlorobenzene can be reduced to 3-chloroaniline with Fe/HCl mixture, the Bechamp reduction.
Chlorobenzene (abbreviated PhCl) is an aryl chloride and the simplest of the chlorobenzenes, consisting of a benzene ring substituted with one chlorine atom. Its chemical formula is C 6 H 5 Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals. [6]
Nitrochlorobenzene is typically synthesized by nitration of chlorobenzene in the presence of sulfuric acid: . C 6 H 5 Cl + HNO 3 → O 2 NC 6 H 4 Cl + H 2 O. This reaction affords a mixture of isomers.
Nitrobenzenes are a group of nitro compounds consisting of one or more nitro groups as substituents on a benzene core. They have the formula C 6 H 6–n (NO 2) n, where n = 1–6 is the number of nitro groups. Depending on the number of nitro groups, there may be several constitutional isomers possible. Mononitrobenzene; Dinitrobenzene. 1,2 ...
Diagram showing the ortho, meta and para positions relative to a substituent X on a benzene ring. Electron donating groups are typically divided into three levels of activating ability (The "extreme" category can be seen as "strong".) Electron withdrawing groups are assigned to similar groupings.
Nucleophiles displace the chloride adjacent to the nitro group: ammonia gives the aniline derivative, aqueous base gives the phenol derivative, and methoxide gives the anisole derivative. These compounds are respectively 4-chloro-2-nitroaniline, 4-chloro-2-nitrophenol, and 4-chloro-2-nitroanisole. [2]
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.