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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]

Additional recommended knowledge

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.

References

     
    This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Chlorobenzene". A list of authors is available in Wikipedia.
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