三(三氟甲磺酰基)甲烷

三(三氟甲磺酰基)甲烷
	IUPAC名; [Bis(trifluoromethanesulfonyl)methanesulfonyl]tri(fluoro)methane
別名	Triflidic acid, tris(triflyl)methane, tris[(trifluoromethyl)sulfonyl]methane
識別
CAS號	60805-12-1
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
性質
化學式	C4F9S3O6H
摩爾質量	412.23 g/mol g·mol⁻¹
外觀	無色固體
熔點	69.2 °C（342 K）
溶解性（水）	混溶
pKa	–18.6（水溶液，推算）
危險性
	GHS危險性符號;
GHS提示詞	危險
H-術語	H314, H318, H335
P-術語	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	腐蝕、眼刺激
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

三(三氟甲磺酰基)甲烷是一種有機化合物，化學式為C₄F₉S₃O₆H，或簡寫為Tf₃CH)，是一種有機超酸。它是已知最強的碳負離子酸之一，其酸性是三氟甲磺酸（pK_a^aq ~ –14）的10⁴倍。它最初於1987年由Konrad Seppelt（英語：Konrad Seppelt）和Turowsky通過下法製得：^[2]

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

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

Tf₃C(MgBr) + H₂SO₄ → Tf₃CH + MgBrHSO₄

它的鑭系金屬鹽相比三氟甲磺酸鹽，路易斯酸性更強。^[3]^[4]它也可以（和其它陽離子）形成離子液體。^[5]

參考文獻

^ 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 (編). Encyclopedia of Reagents for Organic Synthesis. 2004. ISBN 9780470842898. doi:10.1002/047084289X.rn00441.
^ 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.
^ 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.
^ 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 （英語）.
^ 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.

[Barrett-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 (編). 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 （英語）.

[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.

[1]

[2]

[3]

[4]

[5]