三(三氟甲磺酰基)甲烷

三(三氟甲磺酰基)甲烷是一种有机化合物，化学式为C₄F₉S₃O₆H，或简写为Tf₃CH)，是一种有机超酸。它是已知最强的碳负离子酸之一，其酸性是三氟甲磺酸（pK_a^aq ~ –14）的10⁴倍。它最初于1987年由Konrad Seppelt（英语：Konrad Seppelt）和Turowsky通过下法制得：^[2]

Tf₂CH₂ + 2CH₃MgBr → Tf₂C(MgBr)₂ + 2CH₄

Tf₂C(MgBr)₂ + TfF → Tf₃C(MgBr) + MgBrF

Tf₃C(MgBr) + H₂SO₄ → Tf₃CH + MgBrHSO₄

三(三氟甲磺酰基)甲烷
IUPAC名 [Bis(trifluoromethanesulfonyl)methanesulfonyl]tri(fluoro)methane
别名	Triflidic acid, tris(triflyl)methane, tris[(trifluoromethyl)sulfonyl]methane
识别
CAS号	60805-12-1  Y
PubChem	4306514
ChemSpider	3512136
SMILES	[H]C(S(=O)(C(F)(F)F)=O)(S(=O)(C(F)(F)F)=O)S(=O)(C(F)(F)F)=O
InChI	InChI=1S/C4HF9O6S3/c5-2(6,7)20(14,15)1(21(16,17)3(8,9)10)22(18,19)4(11,12)13/h1H
InChIKey	MYIAPBDBTMDUDP-UHFFFAOYSA-N
性质
化学式	C4F9S3O6H
摩尔质量	412.23 g/mol g·mol⁻¹
外观	无色固体
熔点	69.2 °C（342 K）
溶解性（水）	混溶
pKa	–18.6（水溶液，推算）[1]
危险性
GHS危险性符号
GHS提示词	危险
H-术语	H314, H318, H335
P-术语	P260, P261, P264, P271, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P312, P321, P363, P403+233
主要危害	腐蚀、眼刺激
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

它的镧系金属盐相比三氟甲磺酸盐，路易斯酸性更强。^[3][4]它也可以（和其它阳离子）形成离子液体。^[5]

参考文献

1. Barrett, A. G. M.; Braddock, D. C.; Raju, G. S. Tris[(trifluoromethyl)sulfonyl]methane and Related Salts. Charette, André; Bode, Jeffrey; Rovis, Tomislav; Shenvi, Ryan (编). Encyclopedia of Reagents for Organic Synthesis. 2004. ISBN 9780470842898. doi:10.1002/047084289X.rn00441.
2. Turowsky, Lutz; Seppelt, Konrad. Tris[(trifluoromethyl)sulfonyl]methane, HC(SO2CF3)3. Inorganic Chemistry. 1988-06-01, 27 (12): 2135–2137. ISSN 0020-1669. doi:10.1021/ic00285a025.
3. Waller, Francis J.; Barrett, Anthony G. M.; Braddock, D. Christopher; Ramprasad, Dorai; McKinnell, R. Murray; White, Andrew J. P.; Williams, David J.; Ducray, Richard. Tris(trifluoromethanesulfonyl)methide ("Triflide") Anion: Convenient Preparation, X-ray Crystal Structures, and Exceptional Catalytic Activity as a Counterion with Ytterbium(III) and Scandium(III). The Journal of Organic Chemistry. 1999-04-01, 64 (8): 2910–2913. ISSN 0022-3263. PMID 11674365. doi:10.1021/jo9800917.
4. Ishihara, Kazuaki; Hiraiwa, Yukihiro; Yamamoto, Hisashi. Homogeneous Debenzylation Using Extremely Active Catalysts: Tris(triflyl)methane, Scandium(III) Tris(triflyl)methide, and Copper(II) Tris(triflyl)methide. Synlett. 2000-01-01, 2000 (1): 80–82. ISSN 0936-5214. doi:10.1055/s-2000-6436 （英语）.
5. Johansson, Katarina M.; Adebahr, Josefina; Howlett, Patrick C.; Forsyth, Maria; MacFarlane, Douglas R. N-Methyl-N-Alkylpyrrolidinium Bis(perfluoroethylsulfonyl)amide ([NPf2]) and Tris(trifluoromethanesulfonyl)methide ([CTf3]) Salts: Synthesis and Characterization. Australian Journal of Chemistry. 2007-01-01, 60 (1): 57–63. doi:10.1071/ch06299.