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Sigma-Aldrich

Scandium(III) triflate

99%

Sinónimos:

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

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About This Item

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

Nivel de calidad

100

Ensayo

99%

Formulario

powder

idoneidad de la reacción

core: scandium
reagent type: catalyst

cadena 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

Clave InChI

HZXJVDYQRYYYOR-UHFFFAOYSA-K

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Descripción general

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.

Aplicación

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 clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
MKCQ5837
MKCM6818
MKCC1843
MKBV7980V
MKBS7568V

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Okamoto, Y., et al.
Macromolecular Symposia, 183, 83-83 (2002)
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
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
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)
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
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Friedel–Crafts Acylation

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

Friedel–Crafts Acylation

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

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