三氟甲硫醇

三氟甲硫醇
英文名	Trifluoromethanethiol
别名	三氟甲基硫醇
识别
CAS号	1493-15-8
SMILES	FC(S)(F)F;
InChI	1S/CHF3S/c2-1(3,4)5/h5H;
InChIKey	MFLLMKMFWIUACU-UHFFFAOYSA-N
性质
化学式	CF3SH
摩尔质量	102.078 g·mol⁻¹
外观	气体
密度	1.352±0.06 g·cm−3
沸点	−36.7 °C（236.5 K）; −36.99 °C（236.16 K）
溶解性（水）	0.72 g（本征溶解度，pH = 1.96）; 易溶于碱溶液
pKa	2.77±0.10
相关物质
相关化学品	三氟甲醇; 甲硫醇
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

三氟甲硫醇是一种有机硫化合物，化学式为CF₃SH，它是一种硫醇。它最早于1953年被制得。^[4]^[2]

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制备

三氟甲硫醇最初由三氟甲硫醇汞和氯化氢气体的反应制得；后来，人们又发现了硫代碳酰氟和氟化氢气体的反应可以产生三氟甲硫醇。其它方法还有三氟甲基二硫化物和硫化氢在紫外光下的反应：^[4]

CF₃SSCF₃ + H₂S → 2 CF₃SH + S

以及一些三氟甲硫基的一些衍生物的反应：^[5]

CF₃SBr + HBr → CF₃SH + Br₂

3 CF₃SNCO + 6 HI → 3 CF₃SH + 3 I₂ + (HNCO)₃

性质

三氟甲硫醇可以和烯烃或炔烃发生加成反应，如和CF₂=CFCl^[6]、CH₂=CHCl^[7]等物质的反应：

它和N-碘代丁二酰亚胺（NIS）反应，可以得到碘代产物CF₃SI。^[8]

参考文献

[1]
Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2019 ACD/Labs). Retrieved from SciFinder. [2019-8-31]
[2]
Haszeldine, R. N.; Kidu, J. M. 639. Reactions of fluorocarbon radicals. Part XI. Synthesis and some reactions of trifluoromethanethiol and trifluoromethanesulphenyl chloride. Journal of the Chemical Society (Resumed). 1953: 3219. ISSN 0368-1769. doi:10.1039/jr9530003219.
[3]
Dininny, R. E.; Pace, E. L. Thermodynamic Properties of Trifluoromethanethiol from 12°K to Its Boiling Point. Entropy from Molecular and Spectroscopic Data. The Journal of Chemical Physics. 1960, 32 (3): 805–809. ISSN 0021-9606. doi:10.1063/1.1730801.
[4]
Zack, Neil R.; Shreeve, Jean'Ne M. A Convenient Synthesis of Trifluoromethane Thiol. Synthetic Communications. 1974, 4 (4): 233–235. ISSN 0039-7911. doi:10.1080/00397917408062078.
[5]
Haas, Alois. Umsetzungen von Trifluormethylsulfenylisocyanat mit Halogenwasserstoffen. Chemische Berichte. 1965, 98 (6): 1709–1714. ISSN 0009-2940. doi:10.1002/cber.19650980605.
[6]
Knight (Ed.). (2005). Product Class 15: Tetraheterosubstituted Methanes with a Carbon−Halogen Bond （页面存档备份，存于互联网档案馆）. Category 3, Compounds with Four and Three Carbon Heteroatom Bonds. doi:10.1055/sos-sd-018-01314
[7]
Harris, John F. The Free-radical Addition of Trifluoromethanesulfenyl Chloride to Haloölefins. Journal of the American Chemical Society. 1962, 84 (16): 3148–3153. ISSN 0002-7863. doi:10.1021/ja00875a022.
[8]
Minkwitz, R.; Lekies, R. Chemistry of sulfur halides. 7. Trifluoromethyliodosulfane. Zeitschrift fuer Anorganische und Allgemeine Chemie, 1985. 527. pp 161-168. ISSN: 0044-2313.

拓展阅读

Minkwitz, Rolf; Liedtke, Andreas. Darstellung und spektroskopische Charakterisierung von Fluor(trifluormethylsulfenyl)phosphonium-Salzen, CF3SPH2F+MF6-(M = As, Sb) / Preparations and Spectroscopic Characterization of Fluoro(trifluoromethylsulfenyl)phosphonium Salts, CF3SPH2F+MF6- (M = As, Sb). Zeitschrift für Naturforschung B. 1988, 43 (10): 1263–1267. ISSN 1865-7117. doi:10.1515/znb-1988-1009.
Haas, Alois; Radau, Godehard. Perfluoroorganochalcogenyl-ketenes IV. Bis(perfluoroorganochalcogenyl)ketenes (RfE)2C=C=O (Rf = CF₃,C₆F₅; E = S, Se): synthons with a high preparative potential. Journal of Fluorine Chemistry. 1998, 89 (1): 9–18. ISSN 0022-1139. doi:10.1016/S0022-1139(98)00079-7.

[SCI-1] [1]
Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2019 ACD/Labs). Retrieved from SciFinder. [2019-8-31]

[Haszeldine-2] [2]
Haszeldine, R. N.; Kidu, J. M. 639. Reactions of fluorocarbon radicals. Part XI. Synthesis and some reactions of trifluoromethanethiol and trifluoromethanesulphenyl chloride. Journal of the Chemical Society (Resumed). 1953: 3219. ISSN 0368-1769. doi:10.1039/jr9530003219.

[3] [3]
Dininny, R. E.; Pace, E. L. Thermodynamic Properties of Trifluoromethanethiol from 12°K to Its Boiling Point. Entropy from Molecular and Spectroscopic Data. The Journal of Chemical Physics. 1960, 32 (3): 805–809. ISSN 0021-9606. doi:10.1063/1.1730801.

[Zack-4] [4]
Zack, Neil R.; Shreeve, Jean'Ne M. A Convenient Synthesis of Trifluoromethane Thiol. Synthetic Communications. 1974, 4 (4): 233–235. ISSN 0039-7911. doi:10.1080/00397917408062078.

[5] [5]
Haas, Alois. Umsetzungen von Trifluormethylsulfenylisocyanat mit Halogenwasserstoffen. Chemische Berichte. 1965, 98 (6): 1709–1714. ISSN 0009-2940. doi:10.1002/cber.19650980605.

[6] [6]
Knight (Ed.). (2005). Product Class 15: Tetraheterosubstituted Methanes with a Carbon−Halogen Bond （页面存档备份，存于互联网档案馆）. Category 3, Compounds with Four and Three Carbon Heteroatom Bonds. doi:10.1055/sos-sd-018-01314

[7] [7]
Harris, John F. The Free-radical Addition of Trifluoromethanesulfenyl Chloride to Haloölefins. Journal of the American Chemical Society. 1962, 84 (16): 3148–3153. ISSN 0002-7863. doi:10.1021/ja00875a022.

[8] [8]
Minkwitz, R.; Lekies, R. Chemistry of sulfur halides. 7. Trifluoromethyliodosulfane. Zeitschrift fuer Anorganische und Allgemeine Chemie, 1985. 527. pp 161-168. ISSN: 0044-2313.

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