Search
Element Search
Structure Search
Thermo Scientific Chemicals
Hafnium trifluoromethanesulfonate, 98%
CAS: 161337-67-3 | C4H2F12HfO13S4 | 792.758 g/mol
Have Questions?
Change view
Chemical Identifiers
CAS161337-67-3
IUPAC Namehafnium(4+) hydrate tetratrifluoromethanesulfonate
Molecular FormulaC4H2F12HfO13S4
InChI KeyXQJOFTWVKHJLHA-UHFFFAOYSA-J
SMILESO.[Hf+4].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F
View more
Specifications
Specification Sheet
Specification SheetAppearance (Color)White to yellow
FormPowder
Assay (unspecified)≥97.5%
Elemental AnalysisFluorine: 28.69-30.16%
Hafnium trifluoromethanesulfonate is a recyclable catalyst for the mononitration of o-nitrotoluene. It serves as a catalyst for homogeneous methoxycarbonylation and hydrocarboxylation reactions of phenylacetylene. It is also used as a reactant for direct Friedel-Crafts reactions of chromene hemiacetals, aminomethylation reactions under Lewis acidic conditions and prins-type cyclization reactions. It is also involved in the direct polycondensation of lactic acid. Further, it is used in cationic benzylation reactions, chemoselective thioacetalization and transthioacetalization of carbonyl compounds.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
Hafnium trifluoromethanesulfonate is a recyclable catalyst for the mononitration of o-nitrotoluene. It serves as a catalyst for homogeneous methoxycarbonylation and hydrocarboxylation reactions of phenylacetylene. It is also used as a reactant for direct Friedel-Crafts reactions of chromene hemiacetals, aminomethylation reactions under Lewis acidic conditions and prins-type cyclization reactions. It is also involved in the direct polycondensation of lactic acid. Further, it is used in cationic benzylation reactions, chemoselective thioacetalization and transthioacetalization of carbonyl compounds.
Solubility
Soluble in methyl cyanide, dicholomethane, dichloroethane, nitromethane, dioxane, terahydrofuran and toluene.
Notes
Incompatible with strong oxidizing agents. Moisture sensitive.
Hafnium trifluoromethanesulfonate is a recyclable catalyst for the mononitration of o-nitrotoluene. It serves as a catalyst for homogeneous methoxycarbonylation and hydrocarboxylation reactions of phenylacetylene. It is also used as a reactant for direct Friedel-Crafts reactions of chromene hemiacetals, aminomethylation reactions under Lewis acidic conditions and prins-type cyclization reactions. It is also involved in the direct polycondensation of lactic acid. Further, it is used in cationic benzylation reactions, chemoselective thioacetalization and transthioacetalization of carbonyl compounds.
Solubility
Soluble in methyl cyanide, dicholomethane, dichloroethane, nitromethane, dioxane, terahydrofuran and toluene.
Notes
Incompatible with strong oxidizing agents. Moisture sensitive.
RUO – Research Use Only
General References:
- Lewis acid catalyst introduced by Kobayashi, effective at low concentrations under mild conditions in Friedel-Crafts acylation and alkylation reactions: Bull. Chem. Soc. Jpn., 68, 2053 (1995). Efficient catalyst for the Fries rearrangement of phenolic esters to acylphenols: Tetrahedron Lett., 37, 2053 (1996); Bull. Chem. Soc. Jpn., 70, 267 (1997). Superior to lanthanide triflates as catalyst for atom-economic aromatic nitration with a stoichiometric amount of nitric acid in DCM, avoiding the use of sulfuric acid: Tetrahedron Lett., 39, 1641 (1198); Synlett, 57 (2000). Efficient catalyst for allylations of imines with Allyl tri-n-butyl tin, L14087, and of Mannich-type reactions of imines with silyl enol ethers: Synlett, 1099 (1997). For use in combination with a catalytic amount of triflic acid for the Friedel-Crafts acylation of aromatics, see: Tetrahedron Lett., 39, 4697 (1998). For use in the catalytic decarboxylative ß-selective glycosylation via a mixed glycosyl carbonate, see: Synlett, 959 (2004). Catalyzes the conjugate addition of indoles to ɑß-enones: Synlett, 2492 (2005).
- Ishitani, H.; Suzuki, H.; Saito, Y.; Yamashita, Y.; Kobayashi, S. Hafnium Trifluoromethanesulfonate [Hf(OTf)4] as a Unique Lewis Acid in Organic Synthesis. Eur. J. Org. Chem. 2015, 2015 (25), 5485-5499.
- Adams, T. C.; Payette, J. N.; Cheah, J. H.; Movassaghi, M. Concise Total Synthesis of (+)-Luteoalbusins A and B. Org. Lett. 2015, 17 (17), 4268-4271.