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469041

Sigma-Aldrich

Hafnium(IV) trifluoromethanesulfonate hydrate

Synonym(s):

Hafnium(IV) triflate, Hf(OTf)4

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About This Item

Linear Formula:
(CF3SO3)4Hf
CAS Number:
161337-67-3
Molecular Weight:
774.77 (anhydrous basis)
MDL number:
MFCD01321255
UNSPSC Code:
12161600
PubChem Substance ID:
24870553
NACRES:
NA.22

reaction suitability

core: hafnium
reagent type: catalyst

mp

>350 °C (lit.)

SMILES string

FC(F)(F)S(=O)(=O)O[Hf](OS(=O)(=O)C(F)(F)F)(OS(=O)(=O)C(F)(F)F)OS(=O)(=O)C(F)(F)F

InChI

1S/4CHF3O3S.Hf/c4*2-1(3,4)8(5,6)7;/h4*(H,5,6,7);/q;;;;+4/p-4

InChI key

BQYMOILRPDTPPJ-UHFFFAOYSA-J

Application

Catalyst for:
  • Homogeneous methoxycarbonylation and hydrocarboxylation reactions of phenylacetylene
  • Direct Friedel-Crafts reactions of chromene hemiacetals
  • Aminomethylation reactions under Lewis acidic conditions
  • Prins-type cyclization reactions
  • Direct polycondensation of lactic acid
  • Cationic benzylation reactions
  • Chemoselective thioacetalization and transthioacetalization of carbonyl compounds
Excellent and recyclable catalyst for the mononitration of o-nitrotoluene.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Hafnium trifluoromethanesulfonate (Hf (OTf)4) as an efficient catalyst in the fries rearrangement and direct acylation of phenol and naphthol derivatives.
Kobayashi S, et al.
Tetrahedron Letters, 37(12), 2053-2056 (1996)
Waller, F.J. et al.
Tetrahedron Letters, 39, 1641-1641 (1998)
Norio Sakai et al.
The Journal of organic chemistry, 68(2), 483-488 (2003-01-18)
The copper(II) triflate- and hafnium(IV) triflate-catalyzed aminomethylation of indole (2) with an N-silyl-N,O-acetal 1 containing a trichloromethyl group provides the primary amine derivative (3a) in modest yield. When 1 equiv of trimethylchlorosilane (TMSCl) was added to the reaction mixture, the

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Fries Rearrangement

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