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| Names | |
|---|---|
| IUPAC name 1-Chloro-4-nitrobenzene | |
| Other names 4-Chloro-1-nitrobenzene; 4-Chloronitrobenzene; p-Nitrochlorobenzene; PNCBO | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.002.554 
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| KEGG | |
| CompTox Dashboard (EPA) | |
SMILES
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| Properties | |
| Chemical formula | C6H4ClNO2 |
| Molar mass | 157.55 g·mol |
| Appearance | Light yellow solid |
| Density | 1.52 g/cm³ (20 °C) |
| Melting point | 83.6 °C (182.5 °F; 356.8 K) |
| Boiling point | 242.0 °C (467.6 °F; 515.1 K) |
| Solubility in water | Insoluble |
| Solubility in other solvents | Soluble in toluene, ether, acetone, hot ethanol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 N verify (what is ?)
Infobox references
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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.
Preparation
4-Nitrochlorobenzene was originally prepared by the nitration of 4 bromochlorobenzene by Holleman and coworkers:
Currently, 4-nitrochlorobenzene is prepared on an industrial scale from chlorobenzene via phase-transfer catalysis using tungsten or zirconium catalysts:
Applications
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.
References
- 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.
- ^ Nitro Compounds, Aromatic. Ullmann's Encyclopedia of Industrial Chemistry, 7th Ed.; Wiley & Sons: New York, 1997; pp. 18-19