4-Nitrochlorobenzene
| 4-nitrochlorobenzene | |
|---|---|
| File:4-chloronitrobenzene.png | |
| 1-Chloro-4-nitrobenzene | |
| Other names 4-Chloro-1-nitrobenzene; 4-Chloronitrobenzene; p-Nitrochlorobenzene; PNCBO | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 100-00-5 
|
| ChemSpider | 7194 |
| SMILES | Script error: No such module "collapsible list". |
| style="background: #F8EABA; text-align: center;" colspan="2" | 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 |
| style="background: #F8EABA; text-align: center;" colspan="2" | Hazards | |
| MSDS | External MSDS |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| 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.
Preparation
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]
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.[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]
References
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<references />, or <references group="..." />- ↑ 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.
- ↑ 3.0 3.1 Nitro Compounds, Aromatic. Ullmann's Encyclopedia of Industrial Chemistry, 7th Ed.; Wiley & Sons: New York, 1997; pp. 18-19
