Trifluoronitrosomethane
{{Chembox
| Name = Trifluoronitrosomethane
| ImageFileL1 =TFNM.svg
| ImageSizeL1 = 180px
| ImageNameL1 = Skeletal formula of trifluoronitrosomethane
| ImageFileR1 = Trifluoronitrosomethane-3D-spacefill.png
| ImageSizeR1 = 120px
| ImageNameR1 = Space-filling model of trifluoronitrosomethane
| ImageFile2 = Trifluoronitrosomethane.png
| ImageSize2 = 160px
| PIN = Trifluoro(nitroso)methane
| OtherNames = Trifluoro-nitrosomethane
Trifluoro-nitroso-methane
Nitrosotrifluoromethane
|Section1={{Chembox Identifiers
| Abbreviations = TFNM
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 60949
| PubChem = 67630
| EINECS = 206-383-2
| InChI = 1S/CF3NO/c2-1(3,4)5-6
| InChIKey = PGOMVYSURVZIIW-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 334-99-6
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = M9H4YRQ7XZ
}}
|Section2={{Chembox Properties
| C=1 | F=3 | N=1 | O=1
| Appearance = Deep blue gas{{cite journal |last1=Griffin |first1=C. E. |last2=Haszeldine |first2=R. N. |title=279. Perfluoroalkyl derivatives of nitrogen. Part VIII. Trifluoronitrosoethylene and its polymers |journal=Journal of the Chemical Society (Resumed) |date=1960 |pages=1398 |doi=10.1039/JR9600001398}}
Purple solid
| Odor =
| MeltingPtC = -196.6
| BoilingPtC = -85
| Density =
| Solubility =
}}
|Section3=
|Section7={{Chembox Hazards
| ExternalSDS =
| MainHazards = Toxic
| NFPA-H = 3
| NFPA-F = 1
| NFPA-R = 0
| FlashPt =
| HPhrases =
| PPhrases =
| GHS_ref =
| PEL =
| IDLH =
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| LC50 =
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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.{{cite journal |author1-link= Otto Ruff |first1= Otto |last1= Ruff |first2= Manfred |last2= Giese |title= Das Trifluor-nitroso-methan, CF3.NO (III.) |journal= Ber Dtsch Chem Ges |volume= 69 |year= 1936 |issue= 4 |pages= 684–689 |doi= 10.1002/cber.19360690411}} 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.{{cite journal |first= Alexander |last= Senning |title= N-, 0-, and S-trihalomethyl compounds |journal= Chemical Reviews |volume= 65 |year= 1964 |issue= 4 |pages= 385–412 |doi= 10.1021/cr60236a001 }}{{cite journal |first1= C. W. |last1= Taylor |first2= T. J. |last2= Brice |first3= R. L. |last3= Wear |title= The Preparation of Polyfluoronitrosoalkanes from Nitrosyl Polyfluoroacylates |journal= Journal of Organic Chemistry |volume= 27 |year= 1962 |issue= 3 |pages= 1064–1066 |doi= 10.1021/jo01050a523}}{{cite journal |first1= J. D. |last1= Park |first2= R. W. |last2= Rosser |first3= J. R. |last3= Lacher |title= Preparation of Perfluoronitrosoalkanes. Reaction of Trifluoroacetic Anhydride with Nitrosyl Chloride |journal= Journal of Organic Chemistry |volume= 27 |year= 1962 |issue= 4 |pages= 1642 |doi= 10.1021/jo01051a519}}
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.{{Cite book|title=Comprehensive Handbook of Chemical Bond Energies|last=Luo|first=Yu-Ran|publisher=CRC Press|year=2007|isbn=978-0-8493-7366-4|location=Boca Raton, Fl.|pages=406}}
Related
Trifluoronitrosoethylene is also a similar deep blue gas.{{cite journal |last1=Griffin |first1=C. E. |last2=Haszeldine |first2=R. N. |title=279. Perfluoroalkyl derivatives of nitrogen. Part VIII. Trifluoronitrosoethylene and its polymers |journal=Journal of the Chemical Society (Resumed) |date=1960 |pages=1398–1406 |doi=10.1039/JR9600001398}}
See also
References
{{Reflist}}