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 ;
Abbreviations	TFNM
ChemSpider	60949 ;
ECHA InfoCard	100.005.804
EC Number	206-383-2;
PubChem CID	67630;
UNII	M9H4YRQ7XZ ;
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 ; 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 organic compound consisting of a trifluoromethyl group covalently bound to a nitroso group. Its distinctive deep blue color is unusual for a gas.

History

Trifluoronitrosomethane was synthesized for the first time in 1936 by Otto Ruff and Manfred Giese at the University of Wrocław.^[2] It was created through 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% 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

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]

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.
^ 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

Media related to Trifluoronitrosomethane at Wikimedia Commons

[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.

[cr-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.