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Bismuth(III) chloride is used as a catalyst in organic synthesis and to prepare other bismuth salts. It is used as a starting material for the preparation of bismuthoxychloride upon hydrolysis. It is an oxidizing agent to prepare metallic bismuth by reducing agent. Further, it catalyzes the Michael reaction and the Mukaiyama-aldol reaction. In addition to this, it is a Lewis acid.
Lewis acid catalyst which promotes the rearrangement of acetanilides to o-amino ketones: Tetrahedron Lett., 3217 (1976).
Silyl enol ethers can be ɑ-acylated with acyl chlorides in the presence of a catalytic amount of BiCl3 and NaI or ZnI2; other Lewis acids such as ZnCl2 were less effective: J. Org. Chem., 61, 3885 (1996).
Catalyzes the addition of 1,3-dicarbonyl compounds to Michael acceptors under solvent-free conditions with microwave irradiation: Tetrahedron Lett., 38, 1449 (1997).
For catalysis of Diels-Alder and hetero Diels-Alder reactions, see: J. Org. Chem., 62, 4880 (1997); Tetrahedron Lett., 39, 1161 (1998).
Arenes undergo sufonylation by heating with arenesulfonyl chlorides in the presence of BiCl3 (5 mol%) and triflic acid (10 mol%) to give high yields of mixed diaryl sulfones; neither BiCl3 nor TfOH alone is effective: Tetrahedron Lett., 40, 9233 (1999).
Promotes the chemoselective deprotection of N-Boc amino acids and peptides: Tetrahedron Lett., 47, 389 (2006).
For a brief feature on Bi(III) catalysts, see: Synlett, 1194 (2001). For a review of their use in acylation and sulfonylation reactions, see: Synlett, 181 (2002).
Antonio, M. R.; McAlister, D. R.; Horwitz, E. P. An europium(III) diglycolamide complex: insights into the coordination chemistry of lanthanides in solvent extraction. Dalton Trans. 2015, 44 (2), 515-521.
Vuorinen, S.; Lahcini, M.; Hatanpää, T.; Sundberg, M.; Leskelä, M.; Repo, T. Bismuth(III) Alkoxide Catalysts for Ring-Opening Polymerization of Lactides and ε-Caprolactone. Macromol. Chem. Phys. 2013, 214 (6), 707-715.
Hazard Statements: H303-H314-H318
May be harmful if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a
IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.