|Jmol-3D images||Image 1|
|Molar mass||157.55 g mol−1|
|Appearance||Light yellow solid|
|Density||1.52 g/cm³ (20 °C)|
83.6 °C, 357 K, 182 °F
242.0 °C, 515 K, 468 °F
|Solubility in water||Insoluble|
|Solubility in other solvents||Soluble in toluene, ether, acetone, hot ethanol|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
4-Nitrochlorobenzene is the organic compound with the formula ClC6H4NO2. It is a light yellow 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.
4-nitrochlorobenzene is prepared industrially by nitration of chlorobenzene. This reaction affords both the 2-nitro and the 4-nitro derivatives, in a 1:2 ratio. These are separated by distillation. Chlorobenzene undergoes phase-transfer catalysis using tungsten or zirconium catalysts:
4-Nitrochlorobenzene is an intermediate in the preparation of a variety of derivatives, including 4-chloroaniline, 4-nitrophenol, 4-nitroanisole, 4-nitroaniline, 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, 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. It is the precursor to the anti-leprosy drug Dapsone.
- "The nitration of mixed dihalogen benzenes" Recueil des Travaux Chimiques des Pays-Bas et de la Belgique. Amsterdam, 1915; pp. 204-235.
- Zhang, Cun; Liu, Tao; Ma, Chunyan. U.S. Patent 10,235,242, 2008.
- Gerald Booth "Nitro Compounds, Aromatic in Ullmann's Encyclopedia of Industrial Chemistry, 7th Ed.; Wiley-VCH: Weinheim, 2005. doi:10.1002/14356007.a17 411