Bismuth(III) trifluoromethanesulfonate

• Catalog No.: L19687
• CAS Number: 88189-03-1
• M. F.: C3BiF9O9S3
• M. W.: 656.1877288
• Purity: 99%

SYNONYMS

• Title: 三氟甲烷磺酸铋(III)
• IUPAC name: bismuth(3+) ion tritrifluoromethanesulfonate
• IUPAC Traditional name: bismuth(3+) ion tritriflate
• Synonyms: Bismuth triflate; Trifluoromethanesulfonic acid bismuth salt

DATABASE IDS

• CAS Number: 88189-03-1
• MDL Number: MFCD02093669

PROPERTIES

• Purity: 99%
• Melting Point: >300°C
• GHS Hazard statements: H314-H318
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P280-P303+P361+P353-P305+P351+P338-P310
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• Storage Warning: Hygroscopic
• TSCA Listed: 否
• Hazard Class: 8
• UN Number: UN3261
• Packing Group: III

REFERENCES

• Catalyzes the Michael-type addition of a variety of primary and secondary aliphatic amines to ɑ,?-unsaturated compounds (acrylates, etc.) to give the saturated amino derivatives: Synlett, 720 (2003).
• The Ritter reaction of various nitriles with tert-alcohols to give tert-alkyl amides has been accomplished in high yield in the presence if a cataytic acmount of Bi(OTf)₃: Tetrahedron Lett., 47, 8699 (2006).
• It is also effective in inducing a direct catalytic three-component Mannich reaction of an aldehyde, an amine and a ketone in aqueous media to give a ?-amino ketone: Tetrahedron Lett., 47, 8457 (2006).
• Mild Lewis acid catalyst for high-yield acylation of alcohols: Angew. Chem. Int. Ed., 39, 2877 (2000), and Friedel-Crafts acylation of aromatics, effective at 5-10 mol%: Tetrahedron Lett., 38, 8871 (1997); Eur. J. Org. Chem., 2743 (1998). For use in the Claisen rearrangement of allyl ethers and the Fries rearrangement of phenyl esters, see: Synth. Commun., 34, 1433 (2004); Synlett, 2794 (2004); Tetrahedron Lett., 47, 4051 (2006). Aromatic sulfonylation can also be effected with sulfonyl chlorides: J. Org. Chem., 64, 6479 (1999). At 0.1-0.5 mol%, catalyzes the acylation of primary and secondary alcohols with anhydrides in high yield under mild conditions: J. Org. Chem., 66, 8926 (2001); see also Synthesis, 2091 (2001). For a review of acylation and sulfonylation reactions, see: Synlett, 181 (2002).
• Promotes the rearrangement of aryl-substituted epoxides to aldehydes and ketones: Tetrahedron Lett., 42, 8129 (2001). Catalyzes the deprotection of acetals and ketals under mild conditions: J. Org. Chem., 67, 127 (2002), and also the rapid cleavage of thioacetals: Tetrahedron Lett., 44, 2857 (2003). Catalyzes the allylation of aldehydes with Allyltri-n-butyltin, L14087, to give homoallylic alcohols: Synlett, 1694 (2002); J. Org. Chem., 70, 2091 (2005), and of acetals with Allyltrimethylsilane, A14662, providing a mild and efficient route to homoallyl ethers: Tetrahedron Lett., 43, 4597 (2002).
• For a reviews on uses of this reagent in synthesis, see: Synlett, 1566 (2003); Eur. J. Org. Chem., 2517 (2004). For a review of applications of Bi(III) compounds in synthesis, see: Tetrahedron, 58, 8373 (2002).