Chemistry:Trifluoroacetonitrile
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3D model (JSmol)
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| Properties | |
| C2F3N | |
| Molar mass | 95.024 g·mol−1 |
| Appearance | colourless gas[1] |
| Boiling point | −64 °C (1013 hPa)[1] |
| insoluble[1] | |
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Related compounds
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acetonitrile trifluoromethylisocyanide trichloroacetonitrile |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Trifluoroacetonitrile is a nitrile with the chemical formula CF3CN.
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
- ↑ 1.0 1.1 1.2 1.3 Sigma-Aldrich Co., product no. 544078.
- ↑ Marshall H. Parker (2004), "A Convenient Preparation of Trifluoroacetonitrile: Application to the Synthesis of a Novel Pyrimidinone Building Block" (in German), Synthetic Communications 34 (5): pp. 903–907, doi:10.1081/SCC-120028363
- ↑ "Synthesis method for pesticide intermediate trifluoroacetonitrile" (in en). https://patents.google.com/patent/CN103804231A/en.
- ↑ F. Swarts, Bulletin des Sociétés Chimiques Belges, 1922, Vol 31, S. 364–365.
- ↑ R. E. Banks, M. G. Barlow (2007) (in German), Fluorocarbon and Related Chemistry: Volume 1, Royal Society of Chemistry, ISBN 978-1-84755-601-1, https://books.google.com/books?id=6G8oDwAAQBAJ
- ↑ H. F. Shurvell, J. A. Faniran (1970), "The infrared and Raman spectra of solid trifluoroacetonitrile" (in German), Journal of Molecular Spectroscopy 33 (3): pp. 436–447, doi:10.1016/0022-2852(70)90137-2, Bibcode: 1970JMoSp..33..436S
- ↑ Valentine Nenajdenko (2014) (in German), Fluorine in Heterocyclic Chemistry Volume 2: 6-Membered Heterocycles, Springer, ISBN 978-3-319-04435-4, https://books.google.com/books?id=N077AwAAQBAJ
- ↑ Klaus Burger, Ulrike Waßmuth, Friedrich Hein, Silvia Rottegger (1984), "Trifluormethyl-substituierte Pyrimidine aus Enaminen und Trifluoracetonitril" (in German), Liebigs Annalen der Chemie 1984 (5): pp. 991–1002, doi:10.1002/jlac.198419840517
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