三氟甲硫醇四甲基铵

三氟甲硫醇四甲基铵是一种有机硫化合物，化学式为[(CH₃)₄N]SCF₃。它可以用于在有机化合物中引入三氟甲硫基（CF₃S-）。^[3]

三氟甲硫醇四甲基铵
英文名	Tetramethylammonium trifluoromethanethiolate
别名	四甲基三氟甲硫醇铵
识别
CAS号	515823-30-0  Y
SMILES	FC([S-])(F)F.C[N+](C)(C)C
性质
化学式	C5H12F3NS
摩尔质量	175.216 g·mol⁻¹
外观	无色针状晶体[1]
熔点	210 °C（483 K）（分解）[2]
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

制备及反应

三氟甲硫醇四甲基铵可由三甲基三氟甲硅烷、四甲基氟化铵和硫单质在四氢呋喃或乙二醇二甲醚中反应得到：^[2]

8 (CH₃)₃SiCF₃ + S₈ + 8 [(CH₃)₄N]F → 8 [(CH₃)₄N]SCF₃ + 8 (CH₃)₃SiF

它可以和芳基重氮盐反应，得到相应的芳基三氟甲硫醚^[4]；和芳胺反应得到异硫氰酸酯（RNCS）。^[5]

参考文献

1. Roesky, Herbert W. Efficient Preparations of Fluorine Compounds. Chapter 8. Synthesis of Zero-Valent Trifluoromethyl Chalcogenato Derivatives, [NMe₄]ECF₃ (E=S, Se, Te), and Related Compounds. 2012. doi:10.1002/9781118409466.
2. Tyrra, Wieland; Naumann, Dieter; Hoge, Berthold; Yagupolskii, Yurii L. A new synthesis of trifluoromethanethiolates—characterization and properties of tetramethylammonium, cesium and di(benzo-15-crown-5)cesium trifluoromethanethiolates. Journal of Fluorine Chemistry. 2003, 119 (1): 101–107. ISSN 0022-1139. doi:10.1016/S0022-1139(02)00276-2.
3. Kovács, Szabolcs; Bayarmagnai, Bilguun; Goossen, Lukas J. Preparation of Electrophilic Trifluromethylthio Reagents from Nucleophilic Tetramethylammonium Trifluoromethylthiolate. Advanced Synthesis & Catalysis. 2017, 359 (2): 250–254. ISSN 1615-4150. doi:10.1002/adsc.201601298.
4. Bertoli, Giulia; Exner, Benjamin; Evers, Mathies V.; Tschulik, Kristina; Gooßen, Lukas J. Metal-free trifluoromethylthiolation of arenediazonium salts with Me4NSCF3. Journal of Fluorine Chemistry. 2018, 210: 132–136. ISSN 0022-1139. doi:10.1016/j.jfluchem.2018.03.011.
5. Scattolin, Thomas; Pu, Maoping; Schoenebeck, Franziska. Investigation of (Me₄N)SCF₃ as a Stable, Solid and Safe Reservoir for S=CF₂ as a Surrogate for Thiophosgene. Chemistry - A European Journal. 2018, 24 (3): 567–571. ISSN 0947-6539. doi:10.1002/chem.201705240.