Trifluoronitrosomethane
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| Names | |||
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| Preferred IUPAC name
Trifluoro(nitroso)methane | |||
Other names
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| 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 | Blue to deep-blue gas[1] Blue-green 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).
Infobox references
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Trifluoronitrosomethane (commonly abbreviated as TFNM) is a toxic and unstable gaseous compound consisting of a trifluoromethyl group covalently bound to a nitroso group. The gas is notable for its intense blue colour.
Properties
Although it is somewhat more kinetically stable than expected due to its fluorine substituents, trifluoronitrosomethane, like other nitroso compounds, has a C–N bond that is weaker than normal. The bond enthalpy of the C–N bond is only 167 kJ/mol (39.9 kcal/mol).[2]
Production
Trifluoronitrosomethane can be produced from the reaction of trifluoroiodomethane and nitric oxide under a UV light with a yield of up to 90%. A significant amount of mercury metal is needed to quench the iodine and nitrogen dioxide gases produced during the reaction.[3][4]
Pyrolysis of trifluoroacetyl nitrite gives trifluoronitrosomethane with yields over 85%. Carbon dioxide is formed as a side product. This method may also be employed to make other perfluoronitrosoalkanes from the corresponding perfluorocarboxylic acids.[5]
- CF3C(O)ONO → CF3NO + CO2
History
Trifluoronitrosomethane was synthesised for the first time in 1936 by Otto Ruff and Manfred Giese at the Schlesische Friedrich-Wilhelms-Universität zu Breslau.[6] It was formed through a reaction involving the fluorination of silver cyanide in the presence of silver nitrate and silver oxide.
See also
References
- ^ 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.
- ^ Luo, Yu-Ran (2007). Comprehensive Handbook of Chemical Bond Energies. Boca Raton, Fl.: CRC Press. p. 406. ISBN 978-0-8493-7366-4.
- ^ 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.
- ^ 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.
External links
- "Making a Blue Gas You've Never Seen Before – Trifluoronitrosomethane". YouTube. 7 November 2025.
- "Making a Blue Gas Again - But Different". YouTube. 13 December 2025.