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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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250 MG
$54.70
1 G
$68.20
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$171.00

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Estimated to ship onApril 21, 2025FromMILWAUKEE

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250 MG
$54.70
1 G
$68.20
5 G
$171.00

About This Item

Linear Formula:
Sc(SO3CF3)3
CAS Number:
144026-79-9
Molecular Weight:
492.16
Beilstein/REAXYS Number:
8510151
MDL number:
MFCD00192433
UNSPSC Code:
12161600
PubChem Substance ID:
24866212
NACRES:
NA.22

$54.70

Estimated to ship onApril 21, 2025FromMILWAUKEE

Request a Bulk Order

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

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General description

Scandium(III) triflate is an extremely active, efficient, recoverable and reusable acylation catalyst.[1] Its an important catalyst for the Friedel-Crafts acylation, Diels-Alder reactions and other carbon-carbon bond-forming reactions.[2] It also stereochemically catalyzes the radical polymerization of acrylates.[3] 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.[4]

Application

Scandium(III) triflate was used as a catalyst in:
  • Hydrothiolation reaction of aromatic and aliphatic thiols.[5]
  • Selective two-electron reduction of O2 by ferrocene derivatives.[6]
  • Vinylogous Friedel-Crafts alkylation of indoles and pyrroles in water.[7]
  • Synthesis of β-cyanoketones.[8]
  • Combination with triethylsilane to reductively open functionalized pyranoside rings.[9]
  • The key steps of synthesis of bullvalone via a stabilized sulfur ylide.[10]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ5837
MKCM6818
MKCC1843
MKBV7980V
MKBS7568V

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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
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
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)
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Articles

Friedel–Crafts Acylation

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

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