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| Names | |||
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| Preferred IUPAC name Trifluoro(nitroso)methane | |||
Other names
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| Identifiers | |||
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| Abbreviations | TFNM | ||
| ChemSpider |
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| ECHA InfoCard | 100.005.804 | ||
| EC Number |
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| UNII | |||
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| Properties | |||
| CF3NO | |||
| Molar mass | 99.012 g·mol−1 | ||
| Appearance | 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 | Toxic | ||
| NFPA 704 (fire diamond) | |||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Trifluoronitrosomethane (commonly abbreviatedTFNM) is a toxic gaseouscompound consisting of atrifluoromethyl groupcovalently bound to anitroso group. The gas is notable for its blue colour.
Trifluoronitrosomethane was synthesised for the first time in 1936 byOtto Ruff andManfred Giese at theSchlesische Friedrich-Wilhelms-Universität zu Breslau.[2] It was formed through a reaction involving thefluorination ofsilver cyanide in the presence ofsilver nitrate andsilver oxide.
Trifluoronitrosomethane can be produced from the reaction oftrifluoroiodomethane andnitric oxide under aUV light with a yield of up to 90%. A significant amount ofmercury metal is needed to quench theiodine andnitrogen 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]
Although it is somewhat more kinetically stable than expected due to its fluorine substituents, trifluoronitrosomethane, like othernitroso compounds, has a C–N bond that is weaker than normal. Thebond enthalpy of the C–N bond is only 167 kJ/mol (39.9 kcal/mol).[6]
