Scandium(III) trifluoromethanesulfonate

Scandium(III) trifluoromethanesulfonate
Names


IUPAC name Scandium trifluoromethanesulfonate
Identifiers
CAS Registry Number	144026-79-9^Y
ChemSpider	2016319^Y
InChI InChI=1S/3CHF3O3S.Sc/c32-1(3,4)8(5,6)7;/h3(H,5,6,7);/q;;;+3/p-3^Y Key: HZXJVDYQRYYYOR-UHFFFAOYSA-K^Y InChI=1/3CHF3O3S.Sc/c32-1(3,4)8(5,6)7;/h3(H,5,6,7);/q;;;+3/p-3 Key: HZXJVDYQRYYYOR-DFZHHIFOAT
Jmol-3D images	Image
PubChem	2734571
SMILES C(F)(F)(F)S(=O)(=O)[O-].C(F)(F)(F)S(=O)(=O)[O-].C(F)(F)(F)S(=O)(=O)[O-].[Sc+3]
Properties
Chemical formula	C₃F₉O₉S₃Sc
Molar mass	492.16 g/mol
Hazards
MSDS	Oxford MSDS
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Y verify (what is: Y/N?)
Infobox references

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

Scandium triflate is used as a reagent in organic chemistry as a Lewis acid.^[1] Compared to other Lewis acids, this reagent is stable towards water and can often be used in an organic reaction as a true catalyst rather than one used in stoichiometric amounts. The compound is prepared by reaction of scandium oxide with trifluoromethanesulfonic acid.

An example of the scientific use of scandium triflate is the Mukaiyama aldol addition reaction between benzaldehyde and the silyl enol ether of cyclohexanone with an 81% chemical yield.^[2]

References

↑ Deborah Longbottom (1999). "SYNLETT Spotlight 12: Scandium Triflate". Synlett 1999 (12): 2023. doi:10.1055/s-1999-5997.
↑ S. Kobayashi (1999). "Scandium Triflate in Organic Synthesis". Eur. J. Org. Chem. 1999: 15–27. doi:10.1002/(SICI)1099-0690(199901)1999:1<15::AID-EJOC15>3.0.CO;2-B.

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