Trifluoroacetonitrile

Trifluoroacetonitrile is a nitrile with the chemical formula CF3CN.

Trifluoroacetonitrile
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.005.948
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).
Infobox references

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. 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)
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