Scandium trifluoromethanesulfonate Chemical Properties

Melting point:

>300 °C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Water (Slightly)

form 

Powder

color 

White

Water Solubility 

Soluble in water, alcohol and acetonitrile.

Sensitive 

Hygroscopic

Hydrolytic Sensitivity

6: forms irreversible hydrate

BRN 

8510151

Stability:

hygroscopic

InChI

InChI=1S/3CHF3O3S.Sc/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3

InChIKey

HZXJVDYQRYYYOR-UHFFFAOYSA-K

SMILES

C(F)(S([O-])(=O)=O)(F)F.C(F)(F)(F)S([O-])(=O)=O.C(F)(F)(F)S([O-])(=O)=O.[Sc+3]

CAS DataBase Reference

144026-79-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

3-10

Hazard Note 

Irritant

TSCA 

No

HS Code 

28469099

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

Scandium trifluoromethanesulfonate Usage And Synthesis

Description

Scandium trifluoromethanesulfonate, commonly called Scandium(III) triflate, is a chemical compound with formula Sc(SO3CF3)3, a salt consisting of scandium cations Sc3+ and triflate SO3CF3? anions.
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.

Chemical Properties

White powder

Uses

Scandium(III) trifluoromethanesulfonate is widely used as a catalyst in hydrothiolation, selective two-electron reduction of oxygen by ferrocene derivatives and vinylogous Fridel-crafts alkylation of indoles and pyrrole in water. It is involved in the Mukaiyama aldol addition and stereochemically catalyzes the radical polymerization of acrylates. It acts as a Lewis acid catalyst and used in the synthesis of bullvalone via a stabilized sulfur ylide.

Uses

Scandium Triflate is an important catalyst used in Friedel-Crafts acylation, Baylis-Hillman reaction and other carbon-carbon bond forming reactions.

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.

Reactions

2. Water tolerant Lewis acid.
4. Commonly used in a range of Lewis acid catalyzed reactions.
6. Efficient metal source for Lewis acid catalyzed asymmetric reactions.
8. Catalyzes Friedel-Crafts alkylation, acylation and related reactions.
10. Catalyzes various domino- and multi-component processes.
12. Catalyzes electrophilic additions of alpha-diazoesters with ketones.
14. Catalyzes carbon insertion reactions.

Scandium trifluoromethanesulfonate(144026-79-9)Related Product Information

• Trifluoromethanesulfonic acid
• SILVER TRIFLUOROMETHANESULFONATE
• Lithium trifluoromethanesulfonate
• Zinc trifluoromethanesulfonate
• COPPER(II) TRIFLUOROMETHANESULFONATE
• Trifluoromethanesulfonic anhydride
• Trifluoromethanesulfonyl chloride
• Methyl trifluoromethanesulfonate
• SCANDIUM
• Ethyl trifluoromethanesulfonate
• Scandium acetate
• Scandium trifluoride
• Methanesulfonic acid
• Iron(III) trifluoromethanesulfonate
• YTTERBIUM(III) TRIFLATE HYDRATE, 99.90%
• TIN(II) TRIFLUOROMETHANESULFONATE
• YTTRIUM(III) TRIFLUOROMETHANESULFONATE
• ERBIUM (III) TRIFLUOROMETHANESULFONATE
• Scandium Triflate