| 4-nitrochlorobenzene | |
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1-Chloro-4-nitrobenzene |
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Other names
4-Chloro-1-nitrobenzene; 4-Chloronitrobenzene; p-Nitrochlorobenzene; PNCBO |
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| Identifiers | |
| CAS number | 100-00-5 |
| ChemSpider | 7194 |
| KEGG | C14456 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C6H4ClNO2 |
| Molar mass | 157.55 g mol−1 |
| Appearance | Light yellow solid |
| Density | 1.52 g/cm³ (20 °C) |
| Melting point |
83.6 °C, 357 K, 182 °F |
| Boiling point |
242.0 °C, 515 K, 468 °F |
| Solubility in water | Insoluble |
| Solubility in other solvents | Soluble in toluene, ether, acetone, hot ethanol |
| Hazards | |
| MSDS | External MSDS |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
4-Nitrochlorobenzene is the organic compound 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.
4-Nitrochlorobenzene was originally prepared by the nitration of 4 bromochlorobenzene by Holleman and coworkers[1]:
Currently, 4-nitrochlorobenzene is prepared on an industrial scale from chlorobenzene via phase-transfer catalysis using tungsten or zirconium catalysts:[2]
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.[3] 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.[3]