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
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 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
 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).
Infobox references

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

  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. ^ Luo, Yu-Ran (2007). Comprehensive Handbook of Chemical Bond Energies. Boca Raton, Fl.: CRC Press. p. 406. ISBN 978-0-8493-7366-4.
  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. ^ 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.
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