Trifluoronitrosomethane

Trifluoronitrosomethane
Skeletal formula of trifluoronitrosomethane
Skeletal formula of trifluoronitrosomethane
Space-filling model of trifluoronitrosomethane
Space-filling model of trifluoronitrosomethane
Names
Preferred IUPAC name
Trifluoro(nitroso)methane
Other names
Trifluoro-nitrosomethane
Trifluoro-nitroso-methane
Nitrosotrifluoromethane
Identifiers
Abbreviations TFNM
ChemSpider
ECHA InfoCard 100.005.804 Edit this at Wikidata
EC Number
  • 206-383-2
UNII
  • InChI=1S/CF3NO/c2-1(3,4)5-6
    Key: PGOMVYSURVZIIW-UHFFFAOYSA-N
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
 Toxic
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 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

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]

Trifluoronitrosoethylene is also a similar deep blue gas.[7]

See also

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.