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469041

Sigma-Aldrich

Hafnium(IV) trifluoromethanesulfonate hydrate

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Synonym(s):
Hafnium(IV) triflate, Hf(OTf)4
Linear Formula:
(CF3SO3)4Hf
CAS Number:
Molecular Weight:
774.77 (anhydrous basis)
MDL number:
PubChem Substance ID:
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

Related Categories

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

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


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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
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)

Articles

The Fries rearrangement reaction is an organic name reaction which involves the conversion of phenolic esters into hydroxyaryl ketones on heating in the presence of a catalyst. Suitable catalysts for this reaction are Brønsted or Lewis acids such as HF, AlCl3, BF3, TiCl4, or SnCl4. The Fries rearrangement reaction is an ortho, para-selective reaction, and is used in the preparation of acyl phenols. This organic reaction has been named after German chemist Karl Theophil Fries.

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