三氟甲硫醇四甲基铵
| 三氟甲硫醇四甲基铵 | |
|---|---|
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| 英文名 | Tetramethylammonium trifluoromethanethiolate |
| 别名 | 四甲基三氟甲硫醇铵 |
| 识别 | |
| CAS号 | 515823-30-0 
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| SMILES |
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| 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。 | |
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]
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
- ^ 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.
- ^ 2.0 2.1 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.
- ^ 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.
- ^ 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.
- ^ 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.