[L19687] CAS 88189-03-1 | Bismuth(III) trifluoromethanesulfonate, 99%

CAS : 88189-03-1
UN# : UN3261
MDL : MFCD02093669
Hazard Class : 8
Packing Group : III

Other name :

Bismuth triflateTrifluoromethanesulfonic acid bismuth salt

Chemical Properties

Formula : C3BiF9O9S3
Formula weight : 656.19
Melting Point : >300°
Sensitivity : Hygroscopic. Ambient temperatures.
Form : Powder
Solubility : Soluble in organics acetonitrile, dioxane, dimethyl formamide and dimethyl sulfoxide.

Literature References

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). Catalyzes the Michael-type addition of a variety of primary and secondary aliphatic amines to ɑ,ß-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 ß-amino ketone: Tetrahedron Lett., 47, 8457 (2006). For a reviews on uses of this reagent in synthesis, see: Synlett, 1566 (2003); Eur. J. Org. Chem., 2517 (2004). For a review of Application of Bi(III) compounds in synthesis, see: Tetrahedron, 58, 8373 (2002).

Notes

Hygroscopic. Incompatible with strong oxidizing agents.Other References:UN#: UN3261

Grade Specifications

Grade Specifications

Hazard Statements : H314-H318Causes severe skin burns and eye damage.Causes serious eye damage.
Precautionary Statements : P280-P303+P361+P353-P305+P351+P338-P310Wear protective gloves/protective clothing/eye protection/face protection.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.Immediately call a POISON CENTER or doctor/physician.