Benzotrichloride

Benzotrichloride

Skeletal formula of benzotrichloride Ball-and-stick model of the benzotrichloride molecule
Names
IUPAC name (Trichloromethyl)benzene
Other names Toluene trichloride Phenyl chloroform alpha,alpha,alpha-Trichlorotoluene
Identifiers
CAS Number	98-07-7 N
ChemSpider	7089 N 13882366 N
Jmol 3D model	Interactive image
KEGG	C19166 Y
PubChem	7367
RTECS number	XT9275000
UNII	U62VHG99AM Y
InChI InChI=1S/C7H5Cl3/c8-7(9,10)6-4-2-1-3-5-6/h1-5H Y Key: XEMRAKSQROQPBR-UHFFFAOYSA-N Y
SMILES ClC(Cl)(Cl)c1ccccc1
Properties
Chemical formula	C7H5Cl3
Molar mass	195.48
Appearance	Clear liquid
Density	1.3756 g/mL
Melting point	−5.0 °C (23.0 °F; 268.1 K)
Boiling point	220.8 °C (429.4 °F; 493.9 K)
Solubility in water	0.05g/L
Solubility	organic solvents
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Benzotrichloride, also known as trichlorotoluene is an organic compound with the formula C₆H₅CCl₃. It is principally used as an intermediate in the preparation of other chemical products such as dyes.

Production and uses

Benzotrichloride is produced by the free radical chlorination of toluene, catalysed by light or radical initiators such as dibenzoyl peroxide. Two intermediates are observed:

C₆H₅CH₃ + Cl₂ → C₆H₅CH₂Cl + HCl

C₆H₅CH₂Cl + Cl₂ → C₆H₅CHCl₂ + HCl

C₆H₅CHCl₂ + Cl₂ → C₆H₅CCl₃ + HCl

Benzotrichloride is hydrolysed to benzoyl chloride:

C₆H₅CCl₃ + H₂O → C₆H₅C(O)Cl + 2 HCl

It is also transformed into benzotrifluoride, a precursor to pesticides:

C₆H₅CCl₃ + 3 KF → C₆H₅CF₃ + 3 KCl