三氟亚硝基甲烷

三氟亚硝基甲烷
三氟亚硝基甲烷的键线式	三氟亚硝基甲烷的空间填充模型
	IUPAC名; Trifluoro(nitroso)methane; 三氟(亚硝基)甲烷
别名	亚硝基三氟甲烷
识别
CAS号	334-99-6
PubChem	67630
ChemSpider	60949
InChI	1S/CF3NO/c2-1(3,4)5-6;
InChIKey	PGOMVYSURVZIIW-UHFFFAOYSA-N
EINECS	206-383-2
性质
化学式	CF3NO
摩尔质量	99.01 g·mol−1
外观	深蓝色气体; 紫色固体
熔点	-196.6 °C（77 K）
沸点	-85 °C（188 K）
危险性
主要危害	有毒
NFPA 704	1 3 0
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

三氟亚硝基甲烷（通常简称TFNM）是一种有毒的有机化合物，化学式为CF₃NO，由一个三氟甲基与一个亚硝基共价结合而成。它是深蓝色的气体，这种独特的颜色对于气体来说不寻常。

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1936年，弗罗茨瓦夫大学的Otto Ruff和Manfred Giese首次合成了三氟亚硝基甲烷。^[2]它是由硝酸银和氧化银的存在下对氰化银进行氟化反应产生的。

三氟亚硝基甲烷可以由三氟碘甲烷和一氧化氮在紫外光下反应产生，在常压下产量高达90%。需要少量的汞作为催化剂。该反应的结果是碘作为副产物产生。^[3]^[4]^[5]

亚硝酰氯和三氟乙酸酐之间的反应也可以制备三氟亚硝基甲烷。^[6]^[7]

尽管由于其氟取代基，三氟亚硝基甲烷在动力学上更稳定，但与其他亚硝基化合物一样具有弱C-N键，只有39.9 kcal/mol。^[8]

三氯亚硝基甲烷

[1]
Griffin, C. E.; Haszeldine, R. N. 279. Perfluoroalkyl derivatives of nitrogen. Part VIII. Trifluoronitrosoethylene and its polymers. Journal of the Chemical Society (Resumed). 1960: 1398. doi:10.1039/JR9600001398.
[2]
O. Ruff und M. Giese: Das Trifluor-nitroso-methan, CF3NO (III.) In: Ber dtsch Chem Ges 69, 1936, S. 684–689. doi:10.1002/cber.19360690411
[3]
Senning, Alexander. N-, 0-, and S-trihalomethyl compounds. Chemical Reviews. 1964, 65 (4): 385–412. doi:10.1021/cr60236a001.
[4]
Taylor, C. W.; Brice, T. J.; Wear, R. L. The Preparation of Polyfluoronitrosoalkanes from Nitrosyl Polyfluoroacylates. Journal of Organic Chemistry. 1962, 27 (3): 1064–1066. doi:10.1021/jo01050a523.
[5]
Park, J. D.; Rosser, R. W.; Lacher, J. R. Preparation of Perfluoronitrosoalkanes. Reaction of Trifluoroacetic Anhydride with Nitrosyl Chloride. Journal of Organic Chemistry. 1962, 27 (4): 1642. doi:10.1021/jo01051a519.
[6]
Taylor, C. W.; Brice, T. J.; Wear, R. L. The Preparation of Polyfluoronitrosoalkanes from Nitrosyl Polyfluoroacylates. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1962, 27 (3): 1064–1066. ISSN 0022-3263. doi:10.1021/jo01050a523.
[7]
Park, J. D.; Rosser, R. W.; Lacher, J. R. Preparation of Perfluoronitrosoalkanes. Reaction of Trifluoroacetic Anhydride with Nitrosyl Chloride. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1962, 27 (4): 1462–1462. ISSN 0022-3263. doi:10.1021/jo01051a519.
[8]
Luo, Yu-Ran. Comprehensive Handbook of Chemical Bond Energies. Boca Raton, Fl.: CRC Press. 2007: 406. ISBN 978-0-8493-7366-4.

维基共享资源上的相关多媒体资源：三氟亚硝基甲烷

[1] [1]
Griffin, C. E.; Haszeldine, R. N. 279. Perfluoroalkyl derivatives of nitrogen. Part VIII. Trifluoronitrosoethylene and its polymers. Journal of the Chemical Society (Resumed). 1960: 1398. doi:10.1039/JR9600001398.

[2] [2]
O. Ruff und M. Giese: Das Trifluor-nitroso-methan, CF3NO (III.) In: Ber dtsch Chem Ges 69, 1936, S. 684–689. doi:10.1002/cber.19360690411

[cr-3] [3]
Senning, Alexander. N-, 0-, and S-trihalomethyl compounds. Chemical Reviews. 1964, 65 (4): 385–412. doi:10.1021/cr60236a001.

[4] [4]
Taylor, C. W.; Brice, T. J.; Wear, R. L. The Preparation of Polyfluoronitrosoalkanes from Nitrosyl Polyfluoroacylates. Journal of Organic Chemistry. 1962, 27 (3): 1064–1066. doi:10.1021/jo01050a523.

[5] [5]
Park, J. D.; Rosser, R. W.; Lacher, J. R. Preparation of Perfluoronitrosoalkanes. Reaction of Trifluoroacetic Anhydride with Nitrosyl Chloride. Journal of Organic Chemistry. 1962, 27 (4): 1642. doi:10.1021/jo01051a519.

[:0-6] [6]
Taylor, C. W.; Brice, T. J.; Wear, R. L. The Preparation of Polyfluoronitrosoalkanes from Nitrosyl Polyfluoroacylates. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1962, 27 (3): 1064–1066. ISSN 0022-3263. doi:10.1021/jo01050a523.

[:1-7] [7]
Park, J. D.; Rosser, R. W.; Lacher, J. R. Preparation of Perfluoronitrosoalkanes. Reaction of Trifluoroacetic Anhydride with Nitrosyl Chloride. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1962, 27 (4): 1462–1462. ISSN 0022-3263. doi:10.1021/jo01051a519.

[8] [8]
Luo, Yu-Ran. Comprehensive Handbook of Chemical Bond Energies. Boca Raton, Fl.: CRC Press. 2007: 406. ISBN 978-0-8493-7366-4.

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