CAS 88189-03-1 Bismuth(III) trifluoromethanesulfonate

Synonyms

Methanesulfonic acid, 1,1,1-trifluoro-, bismuth(3+) salt (3:1)

IUPAC Name

bismuth;trifluoromethanesulfonate;

Molecular Weight

656.2

Molecular Formula

C3BiF9O9S3

Canonical SMILES

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

InChI

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

Melting Point

300 °C

Purity

99%

Appearance

Liquid

Complexity

145

Covalently-Bonded Unit Count

Exact Mass

655.83647

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

655.83647

Rotatable Bond Count

Topological Polar Surface Area

197 Å²

UNII

51KD8E1741

Application

Bismuth(III) trifluoromethanesulfonate is a powerful Lewis acid that serves a crucial role as a catalyst in various organic synthesis reactions. It facilitates Friedel-Crafts acylation and the cycloisomerization of allene-enol ethers, acting as a direct substitution catalyst. This compound is particularly effective in the substitution of allylic, propargylic, and benzylic alcohols with sulfonamides, carboxamides, and carbamates. Additionally, it is employed in Mukaiyama aldol reactions, showcasing its versatility and importance in chemical processes.

April 9, 2025

Excellent Catalytic Performance in Organic Syntheses

Using Bismuth(III) trifluoromethanesulfonate in our lab, it effectively catalyzed Friedel-Crafts acylation and Mukaiyama aldol reactions. The compound's efficiency as a Lewis acid in these reactions significantly streamlined our synthesis process.