Accéder au contenu
Merck
Toutes les photos(2)

Documents

418218

Sigma-Aldrich

Scandium(III) triflate

99%

Synonyme(s) :

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

Se connecterpour consulter vos tarifs contractuels et ceux de votre entreprise/organisme
Toutes les photos(2)

About This Item

Formule linéaire :
Sc(SO3CF3)3
Numéro CAS:
144026-79-9
Poids moléculaire :
492.16
Numéro Beilstein :
8510151
Numéro MDL:
MFCD00192433
Code UNSPSC :
12161600
ID de substance PubChem :
24866212
Nomenclature NACRES :
NA.22

Pureté

99%

Forme

powder

Pertinence de la réaction

core: scandium
reagent type: catalyst

Chaîne 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

Clé InChI

HZXJVDYQRYYYOR-UHFFFAOYSA-K

Vous recherchez des produits similaires ? Visite Guide de comparaison des produits

Catégories apparentées

Description générale

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

Déjà en possession de ce produit ?

Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Les clients ont également consulté

Slide 1 of 2

1 of 2

Ytterbium(III) trifluoromethanesulfonate hydrate Yb 25-28 % (approx.)

Sigma-Aldrich

405329

Ytterbium(III) trifluoromethanesulfonate hydrate

Magnesium trifluoromethanesulfonate 97%

Sigma-Aldrich

337986

Magnesium trifluoromethanesulfonate

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)
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
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
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
Afficher tous les articles scientifiques apparentés

Articles

Friedel–Crafts Acylation

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

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

Contacter notre Service technique