4-Nitrochlorobenzene is the organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with the formula ClC₆H₄NO₂. This compound is a light yellow crystalline solid that is stable to air. 4-Nitrochlorobenzene is a common intermediate in the industrial production of a number of compounds, including common antioxidants found in rubber.

Preparation

4-Nitrochlorobenzene was originally prepared by the nitration

Nitration

Nitration is a general chemical process for the introduction of a nitro group into a chemical compound. The dominant application of nitration is for the production of nitrobenzene, the precursor to methylene diphenyl diisocyanate...

 of 4 bromochlorobenzene by Holleman and coworkers:

Currently, 4-nitrochlorobenzene is prepared on an industrial scale from chlorobenzene via phase-transfer catalysis using tungsten

Tungsten

Tungsten , also known as wolfram , is a chemical element with the chemical symbol W and atomic number 74.A hard, rare metal under standard conditions when uncombined, tungsten is found naturally on Earth only in chemical compounds. It was identified as a new element in 1781, and first isolated as...

 or zirconium

Zirconium

Zirconium is a chemical element with the symbol Zr and atomic number 40. The name of zirconium is taken from the mineral zircon. Its atomic mass is 91.224. It is a lustrous, grey-white, strong transition metal that resembles titanium...

 catalysts:

Applications

4-Nitrochlorobenzene is an intermediate in the preparation of a variety of derivatives, including 4-chloroaniline

4-Chloroaniline

4-Chloroaniline is a organochlorine compound with the formula ClC6H4NH2. This pale yellow solid is one of several known chloroanilines.-Preparation:4-Chloroaniline is not prepared from aniline, which tends to overchlorinate...

, 4-nitrophenol

4-Nitrophenol

4-Nitrophenol is a phenolic compound that has a nitro group at the opposite position of hydroxy group on the benzene ring.-Properties:...

, 4-nitroanisole, 4-nitroaniline

4-Nitroaniline

4-Nitroaniline, p-nitroaniline or 1-amino-4-nitrobenzene is an organic compound with the formula C6H6N2O2. It is an organic chemical compound, consisting of a phenyl group attached to an amino group which is para to a nitro group. The chemical structure of p-nitroaniline is shown at the right...

, 2,4-dinitrochlorobenzene, and 3,4-dichloronitrobenzene. These reactions mainly involve the nucleophilic displacement of chloride . The electron-withdrawing nature of the appended nitro-group makes the benzene ring especially susceptible to nucleophilic aromatic substitution

Nucleophilic aromatic substitution

right|300px|Aromatic nucleophilic substitutionA nucleophilic aromatic substitution is a substitution reaction in organic chemistry in which the nucleophile displaces a good leaving group, such as a halide, on an aromatic ring...

, unlike related chlorobenzene.

Another major 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.