ytterbium(3+) ion tritrifluoromethanesulfonate

• ChemBase ID: 100622
• Molecular Formular: C3F9O9S3Yb
• Molecular Mass: 620.2613288
• Monoisotopic Mass: 620.79493556
• 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.[Yb+3]
• Canonical SMILES: FC(S(=O)(=O)[O-])(F)F.FC(S(=O)(=O)[O-])(F)F.FC(S(=O)(=O)[O-])(F)F.[Yb+3]
• InChI: InChI=1S/3CHF3O3S.Yb/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3
• InChIKey: AHZJKOKFZJYCLG-UHFFFAOYSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: ytterbium(3+) ion tritrifluoromethanesulfonate
• IUPAC Traditional name: ytterbium(3+) tritriflate; ytterbium(3+) ion tritriflate
• Synonyms: Ytterbium(III) triflate; Ytterbium(III) trifluoromethanesulphonate; Ytterbium(III) trifluoromethanesulfonate hydrate; 三氟甲烷磺酸镱(III)水合物

Database IDs

• CAS Number: 54761-04-5
• MDL Number: MFCD03703499; MFCD06200261
• PubChem SID: 162087350
• PubChem CID: 2733225

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

• Apperance: Powder

Safety Information

• Storage Warning: Corrosive/Hygroscopic
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 98%

REFERENCES

• For a review of developments in lanthanide mediated organic synthesis, see: J. Chem. Soc., Perkin 1, 2727 (2001).
• Water-tolerant and potentially reusable Lewis acid catalyst in a wide variety of reactions. The use of rare earth metal triflates in organic synthesis has been reviewed by S. Kobayashi: Synlett, 689 (1994); Chem. Rev., 102, 2227 (2002). Applications include:
• Aldol reactions of silyl enol ethers in aqueous media: J. Org. Chem., 59, 3590 (1994); Bull. Chem. Soc. Jpn., 67, 2342 (1994); or in organic solvents: Synthesis, 371 (1993). Friedel-Crafts acylations: J. Chem. Soc., Chem. Commun., 1157 (1993). Allylation of aldehydes: Bull. Chem. Soc. Jpn., 67, 2342 (1994). Mannich reactions: J. Chem. Soc., Chem. Commun., 1379 (1995). Hetero Diels-Alder reactions: J. Chem. Soc., Chem. Commun., 1195 (1995). Catalyzes Michael additions to methyl vinyl ketone in water. The reaction rate is dramatically increased (up to 20-fold) by the addition of a catalytic amount of N,N,N',N'-Tetramethylethylenediamine, A12536: J. Org. Chem., 71, 352 (2006).