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Chlorobenzene

Chlorobenzene

IUPAC name	chlorobenzene
Other names	benzene chloride monochlorobenzene Phenyl chloride
Identifiers
CAS number	108-90-7
RTECS number	CZ0175000
SMILES	ClC1=CC=CC=C1
Properties
Molecular formula	C₆H₅Cl
Molar mass	112.56 g/mol
Appearance	colorless liquid
Density	1.11 g/cm³, liquid
Melting point	-45 °C (228 K)
Boiling point	131 °C (404 K)
Solubility in water	low
Solubility in other solvents	most organic solvents
Hazards
R-phrases	10 20 51/53
S-phrases	24/25 61
Flash point	29 °C
Related Compounds
Related compounds	benzene 1,4-dichlorobenzene
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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.^{[citation needed]}

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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.