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Benzotrichloride

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Benzotrichloride
Names
IUPAC name
(Trichloromethyl)benzene
Other names
Toluene trichloride
Phenyl chloroform
alpha,alpha,alpha-Trichlorotoluene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.395 Edit this at Wikidata
KEGG
RTECS number
  • XT9275000
UNII
  • InChI=1S/C7H5Cl3/c8-7(9,10)6-4-2-1-3-5-6/h1-5H checkY
    Key: XEMRAKSQROQPBR-UHFFFAOYSA-N checkY
  • ClC(Cl)(Cl)c1ccccc1
Properties
C7H5Cl3
Molar mass 195.48
Appearance Clear liquid
Density 1.3756 g/mL
Melting point -5.0 °C
Boiling point 220.8 °C
0.05g/L
Solubility organic solvents
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
1
0
Flash point 97.22 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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 + Cl2C6H5CH2Cl + HCl
C6H5CH2Cl + Cl2C6H5CHCl2 + 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.