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418218

Sigma-Aldrich

Scandium(III) triflate

99%

Sinônimo(s):

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

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About This Item

Fórmula linear:
Sc(SO3CF3)3
Número CAS:
144026-79-9
Peso molecular:
492.16
Beilstein:
8510151
Número MDL:
MFCD00192433
Código UNSPSC:
12161600
ID de substância PubChem:
24866212
NACRES:
NA.22

Nível de qualidade

100

Ensaio

99%

forma

powder

adequação da reação

core: scandium
reagent type: catalyst

cadeia de caracteres SMILES

[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

chave InChI

HZXJVDYQRYYYOR-UHFFFAOYSA-K

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Descrição geral

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.

Aplicação

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.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análise (COA)

Lot/Batch Number
MKCM6818
MKCC1843
MKBV7980V
MKBS7568V
MKBK9944V

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Sigma-Aldrich

405329

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Magnesium trifluoromethanesulfonate 97%

Sigma-Aldrich

337986

Magnesium trifluoromethanesulfonate

Kazuaki Ishihara et al.
The Journal of organic chemistry, 61(14), 4560-4567 (1996-07-12)
Scandium trifluoromethanesulfonate (triflate), which is commercially available, is a practical and useful Lewis acid catalyst for acylation of alcohols with acid anhydrides or the esterification of alcohols by carboxylic acids in the presence of p-nitrobenzoic anhydrides. The remarkably high catalytic
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
Saya Kakuda et al.
Journal of the American Chemical Society, 137(9), 3330-3337 (2015-02-11)
Mononuclear copper complexes, [(tmpa)Cu(II)(CH3CN)](ClO4)2 (1, tmpa = tris(2-pyridylmethyl)amine) and [(BzQ)Cu(II)(H2O)2](ClO4)2 (2, BzQ = bis(2-quinolinylmethyl)benzylamine)], act as efficient catalysts for the selective two-electron reduction of O2 by ferrocene derivatives in the presence of scandium triflate (Sc(OTf)3) in acetone, whereas 1 catalyzes
Okamoto, Y., et al.
Macromolecular Symposia, 183, 83-83 (2002)
Jens Oelerich et al.
Organic & biomolecular chemistry, 13(9), 2793-2799 (2015-01-22)
Alkylidene malonates and α,β-unsaturated α'-hydroxyketones are demonstrated to be efficient classes of electrophiles for the scandium(III) triflate/sodium dodecyl sulphate (SDS) catalysed vinylogous Friedel-Crafts alkylation of indoles and pyrroles in water. These substrates contain an easily removable auxiliary group that increases
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Artigos

Friedel–Crafts Acylation

The Friedel–Crafts acylation is the reaction of an arene with acyl chlorides or anhydrides using a strong Lewis acid catalyst. This reaction proceeds via electrophilic aromatic substitution to form monoacylated products.

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