Triflidic acid

Triflidic acid
Names
	IUPAC name Tris[(trifluoromethyl)sulfonyl]methane
	Other names Triflidic acid, tris(triflyl)methane
Identifiers
CAS Number	60805-12-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	3512136 ;
	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 Key: MYIAPBDBTMDUDP-UHFFFAOYSA-N;
	SMILES [H]C(S(=O)(C(F)(F)F)=O)(S(=O)(C(F)(F)F)=O)S(=O)(C(F)(F)F)=O;
Properties
Chemical formula	C4F9S3O6H
Molar mass	412.23 g/mol
Appearance	Colorless solid
Melting point	69.2 °C (156.6 °F; 342.3 K)
Solubility in water	Miscible
Acidity (pKa)	–18.6 (aqueous, est.) [1]
Hazards
Main hazards	Corrosive, eye irritant
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Triflidic acid (IUPAC name: tris[(trifluoromethyl)sulfonyl]methane, abbreviated formula: Tf₃CH) is an organic superacid. It is one of the strongest known carbon acids and is among the strongest Brønsted acids in general, with an acidity exceeded only by the carborane acids. Notably, triflidic acid is estimated to have an acidity 10⁴ times that of triflic acid (pK_a^aq ~ –14), as measured by its acid dissociation constant. It was first prepared in 1987 by Seppelt and Turowsky by the following route:[2]

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

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

(3) Tf₃C(MgBr) + H₂SO₄ → Tf₃CH + MgBrHSO₄

In its anionic form, the lanthanide salts of triflidic acid ("triflides") have been shown to be more efficient Lewis acids than the corresponding triflates.[3][4] The triflide anion has also been employed as the anionic component of ionic liquids.[5]

References

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

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[Barrett-1] Barrett, A. G. M.; Braddock, D. C.; Raju, G. S. "Tris[(trifluoromethyl)sulfonyl]methane and Related Salts" Encyclopedia of Reagents for Organic Synthesis". doi:10.1002/047084289X.rn00441

[2] Turowsky, Lutz; Seppelt, Konrad (1988-06-01). "Tris[(trifluoromethyl)sulfonyl]methane, HC(SO2CF3)3". Inorganic Chemistry. 27 (12): 2135–2137. doi:10.1021/ic00285a025. ISSN 0020-1669.

[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 (1999-04-01). "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. 64 (8): 2910–2913. doi:10.1021/jo9800917. ISSN 0022-3263.

[4] Ishihara, Kazuaki; Hiraiwa, Yukihiro; Yamamoto, Hisashi (2000-01-01). "Homogeneous Debenzylation Using Extremely Active Catalysts: Tris(triflyl)methane, Scandium(III) Tris(triflyl)methide, and Copper(II) Tris(triflyl)methide". Synlett. 2000 (1): 80–82. doi:10.1055/s-2000-6436. ISSN 0936-5214.

[5] Johansson, Katarina M.; Adebahr, Josefina; Howlett, Patrick C.; Forsyth, Maria; MacFarlane, Douglas R. (2007-01-01). "N-Methyl-N-Alkylpyrrolidinium Bis(perfluoroethylsulfonyl)amide ([NPf2]) and Tris(trifluoromethanesulfonyl)methide ([CTf3]) Salts: Synthesis and Characterization". Australian Journal of Chemistry. 60 (1): 57–63. doi:10.1071/ch06299.

Triflidic acid

See also

References