4-Nitrochlorobenzene

4-nitrochlorobenzene
Identifiers
CAS number 100-00-5 YesY
ChemSpider 7194 YesY
KEGG C14456 N
Jmol-3D images Image 1
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
 N (verify) (what is: YesY/N?)
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]:

Preparation.png

Currently, 4-nitrochlorobenzene is prepared on an industrial scale from chlorobenzene via phase-transfer catalysis using tungsten or zirconium catalysts:[2]

Preparation2.png

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]

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References

  1. ^ The nitration of mixed dihalogen benzenes. Recueil des Travaux Chimiques des Pays-Bas et de la Belgique. Amsterdam, 1915; pp. 204-235.
  2. ^ Zhang, Cun; Liu, Tao; Ma, Chunyan. U.S. Patent 10,235,242, 2008.
  3. ^ a b Nitro Compounds, Aromatic. Ullmann's Encyclopedia of Industrial Chemistry, 7th Ed.; Wiley & Sons: New York, 1997; pp. 18-19

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