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Scandium(III) trifluoromethanesulfonate

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Scandium(III) trifluoromethanesulfonate
Names
IUPAC name
Scandium trifluoromethanesulfonate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.157.499
  • InChI=1S/3CHF3O3S.Sc/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3 checkY
    Key: HZXJVDYQRYYYOR-UHFFFAOYSA-K checkY
  • 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
  • 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
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).
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Scandium trifluoromethanesulfonate, commonly called scandium triflate, is the inorganic compound with formula Sc(H2O)8(OTf)3 where OTf is the anion CF3SO3-. It is a salt consisting of scandium aquo complex. The structure of the anhydrous derivative is less certain. Like almost all scandium compounds, this salt is colorless.[1]

Syntheses and structure

The compound is prepared by reaction of scandium oxide with trifluoromethanesulfonic acid. Concentration of these solution gives crystals of the octahydrate salt. According to X-ray crystallography, the octahydrate features a square antiprismatic cation.[2] The hydrated salt can be dehydrated to give anhydrous derivative.[1]

Use in organic synthesis

Scandium triflate is used as a reagent in organic chemistry as a Lewis acid.[1][3][4] Compared to other Lewis acids, this reagent is stable towards water and has been used to catalyze organic reactions.[5]

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.[6]

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

See also

References

  1. Sugiura, Masaharu; Kobayashi, Shu; Ollevier, Thierry (2001). "Scandium Trifluoromethanesulfonate". Encyclopedia of Reagents for Organic Synthesis. pp. 1–10. doi:10.1002/047084289X.rn00165.pub2. ISBN 978-0-470-84289-8.
  2. Boyle, Timothy J.; Sears, Jeremiah M.; Neville, Michael L.; Alam, Todd M.; Young, Victor G. (2015). "Structural Properties of the Acidification Products of Scandium Hydroxy Chloride Hydrate". Inorganic Chemistry. 54 (24): 11831–11841. doi:10.1021/acs.inorgchem.5b02030. PMID 26641309.
  3. Deborah Longbottom (1999). "SYNLETT Spotlight 12: Scandium Triflate". Synlett. 1999 (12): 2023. doi:10.1055/s-1999-5997.
  4. Tolba, Amal Hassan; El-Zohry, Ahmed M.; Khan, Jafar Iqbal; Svobodová, Eva; Chudoba, Josef; Klíma, Jiří; Lušpai, Karol; Pižl, Martin; Šturala, Jiří; Cibulka, Radek (2025-08-22). "Redox-innocent scandium(III) as the sole catalyst in visible light photooxidations". Nature Communications. 16 (1): 7851. doi:10.1038/s41467-025-63233-4. ISSN 2041-1723. PMC 12373787. PMID 40846847.
  5. Sugiura, Masaharu; Kobayashi, Shu; Ollevier, Thierry (2001). "Scandium Trifluoromethanesulfonate". Encyclopedia of Reagents for Organic Synthesis. pp. 1–10. doi:10.1002/047084289X.rn00165.pub2. ISBN 978-0-470-84289-8.
  6. 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.{{cite journal}}: CS1 maint: deprecated archival service (link)