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Bismuth(III) Trifluoromethanesulfonate

CAS 88189-03-1 ≥98%

Bismuth(III) Trifluoromethanesulfonate | CAS 88189-03-1 | ≥98%

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Technical Specifications

CAS Number 88189-03-1
EC / EINECS Number 628-926-6
MDL Number MFCD02093669
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
InChIKey NYENCOMLZDQKNH-UHFFFAOYSA-K
PubChem CID 9917655
Molecular Formula C₃BiF₉O₉S₃
Molecular Weight 656.2 g/mol
Melting Point >300 °C
Solubility Soluble in acetonitrile, 1,4-dioxane, dimethylformamide and dimethyl sulfoxide. Reacts with alcohols and amines, and reacts reversibly with water.
Purity ≥98%
Physical Form White to off-white powder
HS Code 2904.99
Shelf Life Retest period: 36 months from date of manufacture
Storage Conditions Hygroscopic. Store in a tightly closed container, protected from moisture.

Product Description & Scientific Applications

Bismuth(III) triflate, Bi(OTf)3, is a water-tolerant Lewis acid: three bulky, strongly electron-withdrawing triflate groups on one bismuth centre induce a high positive charge on the metal. It replaces corrosive triflic acid in the same reactions, and its low toxicity is the feature supporting its use over tin and lanthanide triflates.

The active species is debated. A low concentration of triflic acid, formed on hydrolysis, may be the true catalyst — reaction with any water present gives triflic acid and bismuth oxide.

Applications and Reactions

  • Friedel–Crafts acylation and sulfonylation: acylates and sulfonylates arenes in place of stoichiometric triflic acid.
  • Acylation of alcohols: acylates sterically demanding, tertiary, acid-labile and base-labile alcohols. Less reactive anhydrides — benzoic, pivalic — work under the same conditions.
  • Acetal chemistry: catalyses both formation and deprotection of acetals, and the formation of acylals.
  • THP protection: forms tetrahydropyranyl ethers solvent-free, and removes them; the tetrahydrate operates at 0.1–1.0 mol% for both directions.
  • Epoxide chemistry: substituted anilines open epoxides on this catalyst, giving secondary or primary alcohols according to the oxirane substituent. Also catalyses epoxide rearrangement.
  • Cycloadditions: Diels–Alder and aza-Diels–Alder.
  • Glycosylation: with N-bromosuccinimide, activates thio- and selenoglycosides.
  • Limits: insoluble in the usual glycosylation solvents, so cosolvents are needed and those affect diastereoselectivity. Ketones give poor yields under conditions that work for aldehydes and acetals.

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Safety Information

Hazard Class Not regulated for transport
Transport Category Not classified as dangerous goods for transport (ADR/IATA/IMDG)

Documentation

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