Chlorobenzene

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Chlorobenzene
Chlorobenzene Chlorobenzene
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]
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
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
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

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.[citation needed]

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.

External links

de:Chlorbenzol eo:Klorbenzolo lv:Hlorbenzols fi:Klooribentseeni


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