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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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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