Trichloroacetonitrile

Chemical compound

Chemical Compound
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Trichloroacetonitrile is a nitrile with the chemical formula CCl_CN. It is a colorless liquid that is used as an intermediate in the synthesis of various chemical compounds.

Synthesis

Trichloroacetonitrile can be synthesized through several methods. One common method involves the reaction of trichloroacetamide with phosphorus pentoxide:

Synthesis of trichloroacetonitrile from trichloroacetamide

Another method involves the chlorination of acetonitrile:

Synthesis of trichloroacetonitrile from acetonitrile

Applications

Trichloroacetonitrile is used as a reagent in organic synthesis. It is particularly useful in the preparation of imidates and glycosyl donors.

Imidate Formation

Trichloroacetonitrile reacts with alcohols to form trichloroacetimidates, which are useful intermediates in organic synthesis:

Formation of trichloroacetimidate

Glycosylation Reactions

Trichloroacetonitrile is used in the synthesis of glycosyl trichloroacetimidates, which are important in the formation of glycosidic bonds:

Synthesis of glycosyl trichloroacetimidate

Safety

Trichloroacetonitrile is a hazardous chemical and should be handled with care. It is toxic if inhaled or ingested and can cause skin and eye irritation.

Related pages

• Nitrile
• Chlorination
• Organic synthesis

Gallery

• 
  Structure of trichloroacetonitrile
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  Synthesis from trichloroacetamide
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  Synthesis from acetonitrile
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  Molecular dimensions
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  Related synthesis
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  Synthesis of 2-chloropyridine
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  Synthesis of hydroxyketone
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  Formation of trichloroacetimidate
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  Glycosyl trichloroacetimidate
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  Octaacetyl trehalose
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  Thiogalactose synthesis