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
N (verify) (what is: Y/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. It is a light yellow 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:

4-nitrochlorobenzene is prepared industrially by nitration of chlorobenzene. This reaction affords both the 2-nitro and the 4-nitro derivatives, in a 1:2 ratio. These are separated by distillation. Chlorobenzene undergoes 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. It is the precursor to the anti-leprosy drug Dapsone.