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Scandium(III) trifluoromethanesulfonate

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Chemical compound
Scandium(III) trifluoromethanesulfonate
Names
IUPAC name Scandium trifluoromethanesulfonate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.157.499 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/3CHF3O3S.Sc/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3Key: HZXJVDYQRYYYOR-UHFFFAOYSA-K
  • InChI=1/3CHF3O3S.Sc/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3Key: HZXJVDYQRYYYOR-DFZHHIFOAT
SMILES
  • C(F)(F)(F)S(=O)(=O).C(F)(F)(F)S(=O)(=O).C(F)(F)(F)S(=O)(=O).
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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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

Scandium triflate is used as a reagent in organic chemistry as a Lewis acid. 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.

Sc(OTf)3-mediated aldol condensation
Sc(OTf)3-mediated aldol condensation

See also

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.
Scandium compounds
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