Benzotrichloride

Benzotrichloride
Names
IUPAC name
(Trichloromethyl)benzene
Other names
Toluene trichloride
Phenyl chloroform
alpha,alpha,alpha-Trichlorotoluene
Identifiers
98-07-7 
ChemSpider 7089 
13882366 
Jmol-3D images Image
KEGG C19166 Yes
PubChem 7367
RTECS number XT9275000
UNII U62VHG99AM Yes
Properties
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)
0.05g/L
Solubility organic solvents
Hazards
R-phrases R45 R22 R23 R37/38 R41
S-phrases S53 S45
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
4
0
Flash point 97.22 °C (207.00 °F; 370.37 K)
420 °C (788 °F; 693 K)
Except where noted otherwise, data is 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.[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.