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418218

Sigma-Aldrich

Scandium(III) triflate

99%

Synonym(s):

Sc(OTf)3, Scandium(III) trifluoromethanesulfonate, Trifluoromethanesulfonic acid scandium(III) salt

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About This Item

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

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

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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.

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000430672
0000430672
MKCW7694
MKCQ5837
MKCM6818

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Giovanni Desimoni et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 14(12), 3630-3636 (2008-02-29)
The asymmetric Friedel-Crafts reaction between a series of substituted indoles 2 a-l and methyl (E)-2-oxo-4-aryl-3-butenoates 3 a-c has been efficiently catalyzed by the scandium(III) triflate complex of (4'S,5'S)-2,6-bis[4'-(triisopropylsilyl)oxymethyl-5'-phenyl-1',3'-oxazolin-2'-yl]pyridine (pybox; 1). Substituted 4-(indol-3-yl)-2-oxo-4-arylbutyric acid methyl esters 4 a-n were usually formed
Mild reductive opening of aryl pyranosides promoted by scandium(III) triflate.
Hua-Li Qin et al.
Journal of the American Chemical Society, 129(1), 38-39 (2007-01-04)
Alex R Lippert et al.
Journal of the American Chemical Society, 128(46), 14738-14739 (2006-11-16)
Oligosubstituted bullvalones were synthesized in eight steps from 2,6-cycloheptadienone via a unique Lewis acid catalyzed intramolecular cyclopropanation of a stabilized sulfur ylide, leading directly to the tetracyclic cage structure. Upon exposure to base, the substituted bullvalones tautomerized to a hydroxybullvalene
Okamoto, Y., et al.
Macromolecular Symposia, 183, 83-83 (2002)
Krzysztof Kuciński et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 21(13), 4940-4943 (2015-02-18)
The first use of a Lewis acid catalyst in the addition reaction of both aromatic and aliphatic thiols to unsaturated organosilicon compounds is reported. In catalytic tests, scandium(III) triflate demonstrates high catalytic activity in this process. Under mild conditions (25 °C
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