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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]
2-Nitrochlorobenzene can be reduced to the 2-chloroaniline with Fe/HCl mixture, the Bechamp reduction. [1]2-Nitrochlorobenzene, like its isomers, is reactive toward nucleophiles, resulting in chloride substitution.
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 ...
In November 2011, the EPA approved certain registrations for PCNB, allowing it back on the market for golf course turf, potato, cotton, ornamental bulb and cole crop uses in the United States. [8] PCNB is used widely as a fungicide in other countries, such as China and Japan, [5] however, "it is no longer approved for use within the European ...
It can also be prepared by chlorination of 1-chloro-4-nitrobenzene. [1] One of the chlorides is reactive toward nucleophiles. Potassium fluoride gives 2-chloro-1-fluoro-4-nitrobenzene, an intermediate in the production of herbicides. With ammonia, one obtains 2-chloro-4-nitroaniline, a precursor to diazo dyes.
The 1,3- isomer is uncommon because it is a meta- compound, while chlorine, like all halogens, is an ortho/para-director in terms of electrophilic aromatic substitution. It is mainly used as a precursor to 1,2-dichloro-4-nitrobenzene , an intermediate in the synthesis of agrochemicals . [ 5 ]