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benzotrichloride

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benzotrichloride

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Also known as α,α,α-trichlorotoluene

Benzotrichloride (BTC), also known as α,α,α-trichlorotoluene, phenyl chloroform or (trichloromethyl)benzene, is an organic compound with the formula C6H5CCl3. Benzotrichloride is an unstable, colorless or somewhat yellowish, viscous, chlorinated hydrocarbon with a penetrating odor. Benzotrichloride is used extensively as a chemical intermediate for products of various classes, i.e. dyes and antimicrobial agents.

Chemical data

Formula
C7H5Cl3
Molecular weight
195.5 g/mol
IUPAC name
trichloromethylbenzene
SMILES
C1=CC=C(C=C1)C(Cl)(Cl)Cl
InChIKey
XEMRAKSQROQPBR-UHFFFAOYSA-N
XLogP
3.7
Polar surface area
0 Ų
H-bond donors
0
H-bond acceptors
0
Formal charge
0

via PubChem

~12 min read

Encyclopedic overview

23 sections
Contents
  • Structure and reactivity
  • Production
  • Regulation
  • Metabolism
  • Toxicity
  • Signs of toxicity
  • Animal toxicity
  • Acute toxicity
  • Inhalation
  • Dermal
  • Oral
  • Repeated dose toxicity
  • Inhalation
  • Dermal
  • Oral
  • Mutagenicity and carcinogenicity
  • Inhalation
  • Dermal
  • Oral
  • Aquatic effects
  • Fertility
  • Mechanism of toxicity
  • References

Benzotrichloride (BTC), also known as α,α,α-trichlorotoluene, phenyl chloroform or (trichloromethyl)benzene, is an organic compound with the formula C6H5CCl3. Benzotrichloride is an unstable, colorless or somewhat yellowish, viscous, chlorinated hydrocarbon with a penetrating odor. Benzotrichloride is used extensively as a chemical intermediate for products of various classes, i.e. dyes and antimicrobial agents.

== Structure and reactivity == Benzotrichloride is a poorly water-soluble, clear to yellowish liquid with a penetrating odor. It hydrolyzes rapidly to benzoic acid and hydrochloric acid with a half life of about 2.4 minutes, thus making the compound unstable in the presence of water. In other chemical reactions, benzotrichloride reacts at the chlorinated α-carbon, for example in substitution reactions. It is used as an intermediate in the synthesis of benzoyl chloride, benzotrifluoride and 2,4-dihydroxybenzophenone which in turn are also intermediates in other reactions: C6H5CCl3 + resorcinol → 2,4-dihydroxybenzophenone C6H5CCl3 + H2O → C6H5C(O)Cl + 2 HCl C6H5CCl3 + 3 KF → C6H5CF3 + 3 KCl

Excerpted from Wikipedia’s “benzotrichloride” article, available under the CC BY-SA 4.0 licence.