bismuth(3+) ion tritrifluoromethanesulfonate

• ChemBase ID: 12044
• Molecular Formular: C3BiF9O9S3
• Molecular Mass: 656.1877288
• Monoisotopic Mass: 655.83647156
• SMILES: [O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[Bi+3]
• Canonical SMILES: FC(S(=O)(=O)[O-])(F)F.FC(S(=O)(=O)[O-])(F)F.FC(S(=O)(=O)[O-])(F)F.[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

NAMES AND DATABASE IDS

Names

• IUPAC name: bismuth(3+) ion tritrifluoromethanesulfonate; λ^5-bismuthio(3+) ion tritrifluoromethanesulfonate
• IUPAC Traditional name: bismuth(3+) ion tritriflate; λ^5-bismuthio(3+) ion tritriflate
• Synonyms: Bismuth(III) trifluoromethanesulfonate; Bismuth triflate; Trifluoromethanesulfonic acid bismuth salt; Bi(OTf)3; Bismuth tris(trifluoromethanesulfonate); Bismuth(III) triflate; Bismuth(III) trifluoromethanesulfonate; 三氟甲烷磺酸铋(III); 三氟甲基磺酸铋(III)

Database IDs

• CAS Number: 88189-03-1
• MDL Number: MFCD02093669
• PubChem SID: 24882545; 160975351
• PubChem CID: 9917655

CALCULATED PROPERTIES

• Acid pKa: -3.4301212
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -1.2283616
• LogD (pH = 7.4): -1.2283617
• Log P: 1.1480371
• Molar Refractivity: 15.8602 cm^3
• Polarizability: 7.460577 Å^3
• Polar Surface Area: 57.2 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: >300 °C(lit.); >300°C

Safety Information

• Storage Warning: Hygroscopic; IRRITANT
• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: III
• Risk Statements: 34; 36/37/38
• Safety Statements: 26; 26-36/37/39-45
• TSCA Listed: false; 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H314-H318; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P303+P361+P353-P305+P351+P338-P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 99%
• Linear Formula: Bi(OSO2CF3)3

DETAILS

Sigma Aldrich - 633305

Application
Catalyzes direct substitution of allylic, propargylic, and benzylic alcohols with sulfonamides, carbamates, and carboxamides.1
Packaging
5, 25 g in glass bottle

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).