Benzotrichloride

Benzotrichloride
IUPAC name (Trichloromethyl)benzene
Other names Toluene trichloride Phenyl chloroform alpha,alpha,alpha-Trichlorotoluene
Identifiers
CAS number	98-07-7 Y
ChemSpider	13882366 Y
UNII	U62VHG99AM Y
KEGG	C19166 Y
RTECS number	XT9275000
Jmol-3D images	Image 1
SMILES ClC(Cl)(Cl)c1ccccc1
InChI InChI=1S/C7H5Cl3/c8-7(9,10)6-4-2-1-3-5-6/h1-5H Y Key: XEMRAKSQROQPBR-UHFFFAOYSA-N Y
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
R-phrases	R45 R22 R23 R37/38 R41
S-phrases	S53 S45
NFPA 704	1 4 0
Flash point	97.22 °C; 207.00 °F; 370.37 K
Autoignition temperature	420 °C; 788 °F; 693 K
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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.^[1][2]

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

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.