三氟甲硫醇

三氟甲硫醇
英文名	Trifluoromethanethiol
別名	三氟甲基硫醇
識別
CAS號	1493-15-8
SMILES	FC(S)(F)F;
InChI	1S/CHF3S/c2-1(3,4)5/h5H;
InChIKey	MFLLMKMFWIUACU-UHFFFAOYSA-N
性質
化學式	CF3SH
摩爾質量	102.078 g·mol⁻¹
外觀	氣體
密度	1.352±0.06 g·cm−3
沸點	−36.7 °C（236.5 K）; −36.99 °C（236.16 K）
溶解性（水）	0.72 g（本徵溶解度，pH = 1.96）; 易溶於鹼溶液
pKa	2.77±0.10
相關物質
相關化學品	三氟甲醇; 甲硫醇
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

三氟甲硫醇是一種有機硫化合物，化學式為CF₃SH，它是一種硫醇。它最早於1953年被製得。^[4]^[2]

製備

三氟甲硫醇最初由三氟甲硫醇汞和氯化氫氣體的反應製得；後來，人們又發現了硫代碳酰氟和氟化氫氣體的反應可以產生三氟甲硫醇。其它方法還有三氟甲基二硫化物和硫化氫在紫外光下的反應：^[4]

CF₃SSCF₃ + H₂S → 2 CF₃SH + S

以及一些三氟甲硫基的一些衍生物的反應：^[5]

CF₃SBr + HBr → CF₃SH + Br₂

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

性質

三氟甲硫醇可以和烯烴或炔烴發生加成反應，如和CF₂=CFCl^[6]、CH₂=CHCl^[7]等物質的反應：

它和N-碘代丁二酰亞胺（NIS）反應，可以得到碘代產物CF₃SI。^[8]

參考文獻

^ ^1.0 ^1.1 ^1.2 Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2019 ACD/Labs). Retrieved from SciFinder. [2019-8-31]
^ ^2.0 ^2.1 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.
^ 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.
^ ^4.0 ^4.1 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.
^ Haas, Alois. Umsetzungen von Trifluormethylsulfenylisocyanat mit Halogenwasserstoffen. Chemische Berichte. 1965, 98 (6): 1709–1714. ISSN 0009-2940. doi:10.1002/cber.19650980605.
^ Knight (Ed.). (2005). Product Class 15: Tetraheterosubstituted Methanes with a Carbon−Halogen Bond （頁面存檔備份，存於網際網路檔案館）. Category 3, Compounds with Four and Three Carbon Heteroatom Bonds. doi:10.1055/sos-sd-018-01314
^ 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.
^ Minkwitz, R.; Lekies, R. Chemistry of sulfur halides. 7. Trifluoromethyliodosulfane. Zeitschrift fuer Anorganische und Allgemeine Chemie, 1985. 527. pp 161-168. ISSN: 0044-2313.

拓展閱讀

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] 1.0 ^1.1 ^1.2 Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2019 ACD/Labs). Retrieved from SciFinder. [2019-8-31]

[Haszeldine-2] 2.0 ^2.1 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.

[Zack-4] 4.0 ^4.1 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 （頁面存檔備份，存於網際網路檔案館）. 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.

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