lanthanum(3+) ion tritrifluoromethanesulfonate

• ChemBase ID: 97940
• Molecular Formular: C3F9LaO9S3
• Molecular Mass: 586.1128288
• Monoisotopic Mass: 585.76242656
• SMILES: S(=O)(=O)([O-])C(F)(F)F.S(=O)(=O)(C(F)(F)F)[O-].S(=O)(=O)(C(F)(F)F)[O-].[La+3]
• Canonical SMILES: FC(S(=O)(=O)[O-])(F)F.FC(S(=O)(=O)[O-])(F)F.FC(S(=O)(=O)[O-])(F)F.[La+3]
• InChI: InChI=1S/3CHF3O3S.La/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3
• InChIKey: WGJJZRVGLPOKQT-UHFFFAOYSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: lanthanum(3+) ion tritrifluoromethanesulfonate
• IUPAC Traditional name: lanthanum(3+) tritriflate; lanthanum(3+) ion tritriflate
• Synonyms: Lanthanum triflate; Lanthanum trifluoromethanesulfonate, anhydrous; Lanthanum trifluoromethanesulphonate 98%; La(OTf)3; Lanthanum tris(trifluoromethanesulfonate); Tris(trifluoromethanesulfonato)lanthanum; Lanthanum(III) triflate; Trifluoromethanesulfonic acid lanthanum salt; Lanthanum(III) trifluoromethanesulfonate; 无水三氟甲基磺酸镧; 三氟甲基磺酸镧(III); 三氟甲磺酸 镧盐; 三氟甲磺酸镧(III)

Database IDs

• CAS Number: 52093-26-2
• MDL Number: MFCD00077560
• Beilstein Number: 9009103
• PubChem SID: 24866932; 24882152; 162084418
• PubChem CID: 2733938

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

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: 26-36; 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H314-H318; H315-H319-H335
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.0% (T); 99%; 99.999% trace metals basis
• Grade: purum
• Linear Formula: (CF3SO3)3La

DETAILS

Sigma Aldrich - 430609

Application
A water-tolerant Lewis acid used in the Aldol reaction of silyl enol ethers with aldehydes.1
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 61560

Other Notes
Preparation of organo-lanthanides from organo-lithiums useful for the synthesis of ketones from amides1; Catalyst for the addition of amines to nitriles yielding amidines2; Catalyst for glycosylations3; Review4

REFERENCES

• Effective catalyst for the Baylis-Hillman reaction, using 1,4-Diazabicyclo[2.2.2]octane, A14003, increasing the rate up to 40-fold: J. Org. Chem., 63, 7183 (1998). Catalyzes Michael additions to methyl vinyl ketone in water: J. Org. Chem., 71, 352 (2006). The uses of rare-earth metal triflates in organic synthesis have been reviewed by S. Kobayashi: Synlett, 689 (1994); Chem. Rev., 102, 2227 (2002).