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633305

Bismuth(III) trifluoromethanesulfonate

Synonym(s):

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

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About This Item

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

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

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK3885
MKCG9327
MKCF9864
MKCD1692
MKBZ8978V

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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
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Global Trade Item Number

SKUGTIN
633305-5G04061832721583
633305-25G04061833510223