Triflidic acid

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Triflidic acid
Triflidic acid
Names
Preferred IUPAC name
[Bis(trifluoromethanesulfonyl)methanesulfonyl]tri(fluoro)methane
Other names
Triflidic acid, tris(triflyl)methane, tris[(trifluoromethyl)sulfonyl]methane
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.258.613 Edit this at Wikidata
  • 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
  • [H]C(S(=O)(C(F)(F)F)=O)(S(=O)(C(F)(F)F)=O)S(=O)(C(F)(F)F)=O
Properties
C4F9S3O6H
Molar mass 412.23 g/mol
Appearance Colorless solid
Melting point 69.2 °C (156.6 °F; 342.3 K)
Miscible
Acidity (pKa) –18.6 (aqueous, est.)[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Corrosive, eye irritant
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H314, H335
P260, P261, P264, P271, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Triflidic acid (IUPAC name: tris[(trifluoromethyl)sulfonyl]methane, abbreviated formula: Tf3CH) is an organic

triflic acid (pKaaq ~ –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]

See also

References

  1. ISBN 9780470842898
    .
  2. ISSN 0020-1669
    .
  3. PMID 11674365
    .
  4. S2CID 196771067
    .
  5. doi:10.1071/ch06299
    .
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