Scandium(III) trifluoromethanesulfonate

Scandium(III) trifluoromethanesulfonate

Names
IUPAC name Scandium trifluoromethanesulfonate
Identifiers
CAS Number	144026-79-9^Y
3D model (JSmol)	Interactive image
ChemSpider	2016319^Y
ECHA InfoCard	100.157.499
PubChem CID	2734571
CompTox Dashboard (EPA)	DTXSID70370368
InChI InChI=1S/3CHF3O3S.Sc/c3*2-1(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/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3 Key: HZXJVDYQRYYYOR-DFZHHIFOAT
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
Safety data sheet (SDS)	Oxford MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) 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 SO
₃CF⁻
₃ 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 organic reactions 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% yield.^[2]

Sc(OTf)₃-mediated aldol condensation

See also

• Lanthanide trifluoromethanesulfonates

References

1. Deborah Longbottom (1999). "SYNLETT Spotlight 12: Scandium Triflate". Synlett. 1999 (12): 2023. doi:10.1055/s-1999-5997.
2. 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. Archived from the original on 2013-01-05.