trichloroacetonitrile

Trichloroacetonitrile is an organic compound with the formula CCl3CN. It is a colourless liquid, although commercial samples often are brownish. It is used commercially as a precursor to the fungicide etridiazole. It is prepared by dehydration of trichloroacetamide. As a bifunctional compound, trichloroacetonitrile can react at both the trichloromethyl and the nitrile group. The electron-withdrawing effect of the trichloromethyl group activates the nitrile group for nucleophilic additions. The high reactivity makes trichloroacetonitrile a versatile reagent, but also causes its susceptibility t

Chemical data

Formula: C2Cl3N
Molecular weight: 144.38 g/mol
IUPAC name: 2,2,2-trichloroacetonitrile
SMILES: C(#N)C(Cl)(Cl)Cl
InChIKey: DRUIESSIVFYOMK-UHFFFAOYSA-N
XLogP: 2.1
Polar surface area: 23.8 Å²
H-bond donors: 0
H-bond acceptors: 1
Formal charge: 0

via PubChem

Wikidata facts

Subclass of: chemical compound
Mass: 142.90963204

Show 5 more facts

boiling point: 85.7
canonical SMILES: C(#N)C(Cl)(Cl)Cl
chemical formula: C₂Cl₃N
Commons category: Trichloroacetonitrile
melting point: -42

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Encyclopedic overview

6 sections

Contents

Synthesis
Properties
Use
''O''-Glycosyl-trichloroacetimidates for the activation of carbohydrates
See also
References

== Synthesis == The production of trichloroacetonitrile by dehydration of trichloroacetamide was first described in 1873 by L. Bisschopinck. Trichloroacetonitrile via trichloracetamide

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