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benzotrichloride
Sign in to saveAlso 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
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Encyclopedic overview
23 sectionsContents
- 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.