Trifluoronitrosomethane

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.

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).

History

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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

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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

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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]

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

See also

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References

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  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.
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