All Photos(1)
Synonym(s):
Bi(OTf)3, Bismuth tris(trifluoromethanesulfonate), Bismuth(III) triflate
Linear Formula:
Bi(OSO2CF3)3
CAS Number:
Molecular Weight:
656.19
MDL number:
UNSPSC Code:
12352300
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Quality Level
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
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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
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.
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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Bismuth (III) triflate in organic synthesis.
Gaspard-Iloughmane H and Le Roux C.
European Journal of Organic Chemistry, 2004(12), 2517-2532 (2004)
Bismuth (III) trifluoromethanesulfonate: An efficient catalyst for the sulfonylation of arenes.
Repichet S, et al.
The Journal of Organic Chemistry, 64, 6479-6482 (1999)
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
Applications of bismuth (III) compounds in organic synthesis.
Leonard NM, et al.
Tetrahedron, 58(42), 8373-8397 (2002)
Raffaele Cucciniello et al.
ChemSusChem, 9(23), 3272-3275 (2016-11-24)
The present work deals with the production of monoalkyl glyceryl ethers (MAGEs) through a new reaction pathway based on the reaction of glycidol and alcohols catalyzed by Lewis acid-based catalysts. Glycidol is quantitatively converted with high selectivity (99 %) into MAGEs
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