Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

633305

Sigma-Aldrich

Bismuth(III) trifluoromethanesulfonate

Synonym(s):

Bi(OTf)3, Bismuth tris(trifluoromethanesulfonate), Bismuth(III) triflate

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
Bi(OSO2CF3)3
CAS Number:
88189-03-1
Molecular Weight:
656.19
MDL number:
MFCD02093669
UNSPSC Code:
12161600
PubChem Substance ID:
24882545
NACRES:
NA.22

Quality Level

100

reaction suitability

core: bismuth
reagent type: catalyst

mp

>300 °C (lit.)

SMILES string

[Bi+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F

InChI

1S/3CHF3O3S.Bi/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3

InChI key

NYENCOMLZDQKNH-UHFFFAOYSA-K

Looking for similar products? Visit Product Comparison Guide

Application

Bismuth(III) trifluoromethanesulfonate may be used as a catalyst in the following processes:
  • deprotection of acetals
  • cleavage of 2-tert-butoxy derivatives of thiophenes and furans
  • allylation of acetals to form homoallyl ethers
It may also be used as a substitute to corrosive triflic acid in Friedel-Crafts (FC) acylation and sulfonylation of arenes.
Catalyzes direct substitution of allylic, propargylic, and benzylic alcohols with sulfonamides, carbamates, and carboxamides.

Packaging

Bismuth(III) trifluoromethanesulfonate is an eco-friendly Lewis acid that can be prepared by reacting triflic acid with bismuth(III) trifluoroacetate.

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Bismuth (III) trifluoromethanesulfonate: An efficient catalyst for the sulfonylation of arenes.
Repichet S, et al.
The Journal of Organic Chemistry, 64, 6479-6482 (1999)
Bismuth (III) triflate in organic synthesis.
Gaspard-Iloughmane H and Le Roux C.
European Journal of Organic Chemistry, 2004(12), 2517-2532 (2004)
Maria Ricciardi et al.
ChemSusChem, 10(10), 2291-2300 (2017-04-05)
The disposal of any waste by recovering it within the production plant represents the ultimate goal of every biorefinery. In this scenario, the selective preparation of monoalkyl glyceryl ethers (MAGEs) starting from glycidol, obtained as byproduct in the epichlorohydrin production
Bismuth-catalyzed direct substitution of the hydroxy group in alcohols with sulfonamides, carbamates, and carboxamides.
Hongbo Qin et al.
Angewandte Chemie (International ed. in English), 46(3), 409-413 (2006-12-06)
Applications of bismuth (III) compounds in organic synthesis.
Leonard NM, et al.
Tetrahedron, 58(42), 8373-8397 (2002)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service