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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) triflate in organic synthesis.
Gaspard-Iloughmane H and Le Roux C.
European Journal of Organic Chemistry, 2004(12), 2517-2532 (2004)
Applications of bismuth (III) compounds in organic synthesis.
Leonard NM, et al.
Tetrahedron, 58(42), 8373-8397 (2002)
Bismuth (III) trifluoromethanesulfonate: An efficient catalyst for the sulfonylation of arenes.
Repichet S, et al.
The Journal of Organic Chemistry, 64, 6479-6482 (1999)
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Global Trade Item Number

SKUGTIN
633305-25G04061833510223
633305-5G04061832721583