4-Nitrochlorobenzene

4-nitrochlorobenzene
IUPAC name 1-Chloro-4-nitrobenzene
Other names 4-Chloro-1-nitrobenzene; 4-Chloronitrobenzene; p-Nitrochlorobenzene; PNCBO
Identifiers
CAS number	100-00-5 Y
ChemSpider	7194 Y
KEGG	C14456 N
Jmol-3D images	Image 1
SMILES ClC1=CC=C([N+]([O-])=O)C=C1
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
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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.

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

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