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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: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant