Chlorobenzene

Template:Chembox header | Chlorobenzene
Chlorobenzene Chlorobenzene
Template:Chembox header | General
Systematic name	chlorobenzene
Other names	benzene chloride monochlorobenzene Phenyl chloride
Molecular formula	C6H5Cl
SMILES	ClC1=CC=CC=C1
Molar mass	112.56 g/mol
Appearance	colorless liquid
CAS number	[108-90-7]
Template:Chembox header | Properties
Density and phase	1.11 g/cm³, liquid
Solubility in water	low
Other solvents	most organic solvents
Melting point	-45 °C (228 K)
Boiling point	131 °C (404 K)
Refractive index (nD20)	1.525
Viscosity	? cP at ? °C
Template:Chembox header | Hazards
MSDS	External MSDS
Main hazards	?
NFPA 704
Flash point	29 °C
R/S statement	R: 10 20 51/53 S: 24/25 61
RTECS number	CZ0175000
Template:Chembox header | Related compounds
Related compounds	benzene 1,4-dichlorobenzene
Template:Chembox header | Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Overview

Chlorobenzene is an aromatic organic compound with the chemical formula C₆H₅Cl. It is a colorless, flammable liquid first made in 1851 by reacting phenol and phosphorus pentachloride.

Uses

Chlorobenzene has been used in the manufacture of certain pesticides, most notably DDT by reaction with chloral (trichloroacetaldehyde). It once found use in the production of phenol. Today the major use of chlorobenzene is as an intermediate in the production of nitrochlorobenzenes and diphenyl oxide, which are important in the production of commodities such as herbicides, dyestuffs, and rubber. Chlorobenzene is also used as a high-boiling solvent in organic synthesis as well as many industrial applications.

Synthesis

Chlorobenzene is prepared by chlorination of benzene, usually in the presence of a catalytic amount of Lewis acid such as ferric chloride:

C₆H₆ + Cl₂ → C₆H₅Cl + HCl

Because chlorine is electronegative, PhCl exhibits decreased susceptibility to attack by other electrophiles. For this reason, the chlorination process produces only small amounts of dichloro- and trichlorobenzenes.