Trifluoronitrosomethane
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name
Trifluoro(nitroso)methane | |||
| Other names
Trifluoro-nitrosomethane
Trifluoro-nitroso-methane Nitrosotrifluoromethane | |||
| Identifiers | |||
| Abbreviations | TFNM | ||
| ChemSpider | |||
| ECHA InfoCard | 100.005.804 | ||
| EC Number |
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PubChem CID
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| UNII | |||
CompTox Dashboard (EPA)
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| Properties | |||
| CF3NO | |||
| Molar mass | 99.012 g·mol−1 | ||
| Appearance | Deep blue gas[1] Purple solid | ||
| Melting point | −196.6 °C (−321.9 °F; 76.5 K) | ||
| Boiling point | −85 °C (−121 °F; 188 K) | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards
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Toxic | ||
| NFPA 704 (fire diamond) | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Trifluoronitrosomethane (commonly abbreviated TFNM) is a toxic organic compound consisting of a trifluoromethyl group covalently bound to a nitroso group. Its distinctive deep blue color is unusual for a gas.
History
[edit]Trifluoronitrosomethane was synthesized for the first time in 1936 by Otto Ruff and Manfred Giese at the Schlesische Friedrich-Wilhelms-Universität zu Breslau.[2] It was created through the fluorination of silver cyanide in the presence of silver nitrate and silver oxide.
Production
[edit]Trifluoronitrosomethane can be produced from the reaction of trifluoroiodomethane and nitric oxide under a UV light with a yield of up to 90% in normal pressure. A small amount of mercury is needed as catalyst. The reaction results in the creation of iodine as a by-product.[3][4][5]
Properties
[edit]Although it is somewhat more kinetically stable due to its fluorine substituents, trifluoronitrosomethane, like other nitroso compounds, has a weak C–N bond of only 39.9 kcal/mol.[6]
Related
[edit]Trifluoronitrosoethylene is also a similar deep blue gas.[7]
See also
[edit]References
[edit]- ^ Griffin, C. E.; Haszeldine, R. N. (1960). "279. Perfluoroalkyl derivatives of nitrogen. Part VIII. Trifluoronitrosoethylene and its polymers". Journal of the Chemical Society (Resumed): 1398. doi:10.1039/JR9600001398.
- ^ Ruff, Otto; Giese, Manfred (1936). "Das Trifluor-nitroso-methan, CF3.NO (III.)". Ber Dtsch Chem Ges. 69 (4): 684–689. doi:10.1002/cber.19360690411.
- ^ Senning, Alexander (1964). "N-, 0-, and S-trihalomethyl compounds". Chemical Reviews. 65 (4): 385–412. doi:10.1021/cr60236a001.
- ^ Taylor, C. W.; Brice, T. J.; Wear, R. L. (1962). "The Preparation of Polyfluoronitrosoalkanes from Nitrosyl Polyfluoroacylates". Journal of Organic Chemistry. 27 (3): 1064–1066. doi:10.1021/jo01050a523.
- ^ Park, J. D.; Rosser, R. W.; Lacher, J. R. (1962). "Preparation of Perfluoronitrosoalkanes. Reaction of Trifluoroacetic Anhydride with Nitrosyl Chloride". Journal of Organic Chemistry. 27 (4): 1642. doi:10.1021/jo01051a519.
- ^ Luo, Yu-Ran (2007). Comprehensive Handbook of Chemical Bond Energies. Boca Raton, Fl.: CRC Press. p. 406. ISBN 978-0-8493-7366-4.
- ^ Griffin, C. E.; Haszeldine, R. N. (1960). "279. Perfluoroalkyl derivatives of nitrogen. Part VIII. Trifluoronitrosoethylene and its polymers". Journal of the Chemical Society (Resumed): 1398–1406. doi:10.1039/JR9600001398.
External links
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Media related to Trifluoronitrosomethane at Wikimedia Commons
