Trifluoronitrosomethane

Trifluoronitrosomethane

Skeletal formula of trifluoronitrosomethane Space-filling model of trifluoronitrosomethane
Names
Preferred IUPAC name Trifluoro(nitroso)methane
Other names Trifluoro-nitrosomethane Trifluoro-nitroso-methane Nitrosotrifluoromethane
Identifiers
CAS Number	334-99-6  Y
Abbreviations	TFNM
ChemSpider	60949  Y
ECHA InfoCard	100.005.804
EC Number	206-383-2
PubChem CID	67630
UNII	M9H4YRQ7XZ  Y
CompTox Dashboard (EPA)	DTXSID3073896
InChI InChI=1S/CF3NO/c2-1(3,4)5-6 Key: PGOMVYSURVZIIW-UHFFFAOYSA-N
Properties
Chemical formula	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	Toxic
NFPA 704 (fire diamond)	3 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Trifluoronitrosomethane (commonly abbreviated TFNM) is a toxic gaseous compound consisting of a trifluoromethyl group covalently bound to a nitroso group. The gas is notable for its cyan colour.

History

Trifluoronitrosomethane was synthesised for the first time in 1936 by Otto Ruff and Manfred Giese at the Schlesische Friedrich-Wilhelms-Universität zu Breslau. ^[2] It was formed through a reaction involving the fluorination of silver cyanide in the presence of silver nitrate and silver oxide.

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 vapour and nitrogen dioxide gas 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

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). ^[6] The gas is notable for its cyan color, similar to the blue of trifluoronitrosoethylene. ^[7]

See also

• Chemistry portal

• Hexafluorothioacetone
• Trichloronitrosomethane

References

1. 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.
2. 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.
3. Senning, Alexander (1964). "N-, 0-, and S-trihalomethyl compounds". Chemical Reviews . 65 (4): 385–412. doi:10.1021/cr60236a001.
4. 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.
5. 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.
6. Luo, Yu-Ran (2007). Comprehensive Handbook of Chemical Bond Energies. Boca Raton, Fl.: CRC Press. p. 406. ISBN   978-0-8493-7366-4.
7. 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.