418218

Scandium(III) triflate

99%

• Synonym(s): Sc(OTf)3, Scandium(III) trifluoromethanesulfonate, Trifluoromethanesulfonic acid scandium(III) salt
• Linear Formula: Sc(SO₃CF₃)₃
• CAS Number: 144026-79-9
• Molecular Weight: 492.16
• Beilstein: 8510151
• MDL number: MFCD00192433
• UNSPSC Code: 12161600
• PubChem Substance ID: 24866212
• NACRES: NA.22

Properties

• Quality Level: 100
• Assay: 99%
• form: powder
• reaction suitability: core: scandium; reagent type: catalyst
• SMILES string: [Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F
• InChI: 1S/3CHF3O3S.Sc/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3
• InChI key: HZXJVDYQRYYYOR-UHFFFAOYSA-K

Description

General description

Scandium(III) triflate is an extremely active, efficient, recoverable and reusable acylation catalyst. Its an important catalyst for the Friedel-Crafts acylation, Diels-Alder reactions and other carbon-carbon bond-forming reactions. It also stereochemically catalyzes the radical polymerization of acrylates. Scandium(III) triflate complex of (4′S,5′S)-2,6-bis[4′-(triisopropylsilyl)oxymethyl-5′-phenyl-1′,3′-oxazolin-2′-yl]pyridine has been employed as catalyst for the asymmetric Friedel-Crafts reaction between substituted indoles and methyl (E)-2-oxo-4-aryl-3-butenoates.

Application

Scandium(III) triflate was used as a catalyst in:

• Hydrothiolation reaction of aromatic and aliphatic thiols.
• Selective two-electron reduction of O₂ by ferrocene derivatives.
• Vinylogous Friedel-Crafts alkylation of indoles and pyrroles in water.
• Synthesis of β-cyanoketones.
• Combination with triethylsilane to reductively open functionalized pyranoside rings.
• The key steps of synthesis of bullvalone via a stabilized sulfur ylide.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves