Trifluoracetonitrile

Trifluoroacetonitrile

Trifluoroacetonitrile

Chemical compound

Trifluoroacetonitrile is a nitrile with the chemical formula CF3CN.

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Production

Trifluoroacetonitrile can be produced by dehydration of trifluoroacetamide with trifluoroacetic anhydride in pyridine or carbon tetrachloride.[2][3] This synthesis route was first described by Frédéric Swarts in 1922.[4]

Trifluoroacetonitrile can also be produced by reacting 1,1,1-trichloro-2,2,2-trifluoroethane and ammonia at 610 °C.[5]

Properties

Trifluoroacetonitrile is a colourless gas that is insoluble in water.[1] Solid trifluoroacetonitrile's crystal structure is orthorhombic.[6]

Uses

Trifluoroacetonitrile can be used to prepare other chemicals such as 3-(trifluoromethyl)isoquinoline and 2,4-bis(trifluoromethyl)pyrimidine.[7][8]

References

  1. [1]
    Sigma-Aldrich Co., product no. 544078.
  2. [2]
    Marshall H. Parker (2004), "A Convenient Preparation of Trifluoroacetonitrile: Application to the Synthesis of a Novel Pyrimidinone Building Block", Synthetic Communications (in German), vol. 34, no. 5, pp. 903–907, doi:10.1081/SCC-120028363, S2CID 97226252
  3. [3]
    "Synthesis method for pesticide intermediate trifluoroacetonitrile". google.com.
  4. [4]
    F. Swarts, Bulletin des Sociétés Chimiques Belges, 1922, Vol 31, S. 364–365.
  5. [5]
    R. E. Banks, M. G. Barlow (2007), Fluorocarbon and Related Chemistry: Volume 1 (in German), Royal Society of Chemistry, ISBN 978-1-84755-601-1
  6. [6]
    H. F. Shurvell, J. A. Faniran (1970), "The infrared and Raman spectra of solid trifluoroacetonitrile", Journal of Molecular Spectroscopy (in German), vol. 33, no. 3, pp. 436–447, Bibcode:1970JMoSp..33..436S, doi:10.1016/0022-2852(70)90137-2
  7. [7]
    Valentine Nenajdenko (2014), Fluorine in Heterocyclic Chemistry Volume 2: 6-Membered Heterocycles (in German), Springer, ISBN 978-3-319-04435-4
  8. [8]
    Klaus Burger, Ulrike Waßmuth, Friedrich Hein, Silvia Rottegger (1984), "Trifluormethyl-substituierte Pyrimidine aus Enaminen und Trifluoracetonitril", Liebigs Annalen der Chemie (in German), vol. 1984, no. 5, pp. 991–1002, doi:10.1002/jlac.198419840517{{citation}}: CS1 maint: multiple names: authors list (link)
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