Benzotrichloride

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Benzotrichloride
IUPAC name	(Trichloromethyl)benzene
Other names	Toluene trichloride Phenyl chloroform alpha,alpha,alpha-Trichlorotoluene
Identifiers
CAS number	[98-07-7]
RTECS number	XT9275000
SMILES	ClC(Cl)(Cl)C1=CC=CC=C1
Properties
Molecular formula	C7H5Cl3
Molar mass	195.48
Appearance	Clear liquid
Density	1.3756 g/mL
Melting point	-5.0 °C
Boiling point	220.8 °C
Solubility in water	0.05g/L
Solubility	organic solvents
Hazards
NFPA 704	1 3 0
R-phrases	R45 R22 R23 R37/38 R41
S-phrases	S53 S45
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Benzotrichloride, 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.^[1][2]

[edit] 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:^[3]

C₆H₅CCl₃ + H₂O → C₆H₅C(O)Cl + 2 HCl

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

C₆H₅CCl₃ + 3 KF → C₆H₅CF₃ + 3 KCl

[edit] References

1. ^ Merck Index, 11th Edition, 1120.
2. ^ Benzotrichloride Data page at Inchem.org
3. ^ Manfred Rossberg, Wilhelm Lendle, Gerhard Pfleiderer, Adolf Tögel, Eberhard-Ludwig Dreher, Ernst Langer, Heinz Rassaerts, Peter Kleinschmidt, Heinz Strack, Richard Cook, Uwe Beck, Karl-August Lipper, Theodore R. Torkelson, Eckhard Löser, Klaus K. Beutel, “Chlorinated Hydrocarbons” in Ullmann’s Encyclopedia of Chemical Technology, 2007 John Wiley & Sons: New York.