Trifluoroacetonitrile

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Trifluoroacetonitrile is a nitrile with the chemical formula CF3CN.

Trifluoroacetonitrile
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.005.948 Edit this at Wikidata
EC Number
  • 206-542-6
  • InChI=1S/C2F3N/c3-2(4,5)1-6
    Key: SFFUEHODRAXXIA-UHFFFAOYSA-N
  • FC(F)(F)C#N
Properties
C2F3N
Molar mass 95.024 g·mol−1
Appearance colourless gas[1]
Boiling point −64 °C (1013 hPa)[1]
insoluble[1]
Related compounds
Related compounds
acetonitrile
trifluoromethylisocyanide
trichloroacetonitrile
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Production

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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

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

Uses

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

References

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  1. ^ a b c d Sigma-Aldrich Co., product no. 544078.
  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. ^ "Synthesis method for pesticide intermediate trifluoroacetonitrile". google.com.
  4. ^ F. Swarts, Bulletin des Sociétés Chimiques Belges, 1922, Vol 31, S. 364–365.
  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. ^ 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. ^ Valentine Nenajdenko (2014), Fluorine in Heterocyclic Chemistry Volume 2: 6-Membered Heterocycles (in German), Springer, ISBN 978-3-319-04435-4
  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)