Benzotrichloride

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ImageFile = Benzotrichloride.png ImageSize = 120px
IUPACName = (Trichloromethyl)benzene
OtherNames = Toluene trichloride
Phenyl chloroform
alpha,alpha,alpha-Trichlorotoluene
Section1 = Chembox Identifiers
Abbreviations =
CASNo = 98-07-7
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SMILES = ClC(Cl)(Cl)C1=CC=CC=C1
InChI =
RTECS = XT9275000
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Section2 = Chembox Properties
Formula = C₇H₅Cl₃
MolarMass = 195.48
Appearance = Clear liquid
Density = 1.3756 g/mL
MeltingPt = -5.0 °C
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BoilingPt = 220.8 °C
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Solubility = 0.05g/L
SolubleOther = organic solvents
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Section7 = Chembox Hazards
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NFPA-H = 3
NFPA-F = 1
NFPA-R = 0
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RPhrases = R45 R22 R23 R37/38 R41
SPhrases = S53 S45
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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."Merck Index", 11th Edition, 1120.] [ [http://www.inchem.org/documents/icsc/icsc/eics0105.htm Benzotrichloride] Data page at Inchem.org]

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: [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.] : C₆H₅CCl₃ + H₂O → C₆H₅C(O)Cl + 2 HClIt is also transformed into benzotrifluoride, a precursor to pesticides:: C₆H₅CCl₃ + 3 KF → C₆H₅CF₃ + 3 KCl

References