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.

Preparation

Scandium triflate (Scandium trifluoromethanesulfonate) can be prepared from the corresponding oxide (Sc2O3) and aqueous trifluoromethanesulfonic acid (TfOH). After filtration and concentration of the clear aqueous solution in vacuo, the resulting hydrated salt is dried in vacuo (<1 mmHg) at 200?°C for 40 h to afford the anhydrous triflate stored over P2O5.

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