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三(三氟甲磺酰基)甲烷

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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  checkY
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 混溶
pKa –18.6(水溶液,推算)[1]
危险性
GHS危险性符号
《全球化学品统一分类和标签制度》(简称“GHS”)中腐蚀性物质的标签图案《全球化学品统一分类和标签制度》(简称“GHS”)中有害物质的标签图案
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。

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(pKaaq ~ –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

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.