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Zinc triflate

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Zinc triflate
Names
IUPAC name zinc trifluoromethanesulfonate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.053.548 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/2CHF3O3S.Zn/c2*2-1(3,4)8(5,6)7;/h2*(H,5,6,7);/q;;+2/p-2Key: CITILBVTAYEWKR-UHFFFAOYSA-L
  • InChI=1/2CHF3O3S.Zn/c2*2-1(3,4)8(5,6)7;/h2*(H,5,6,7);/q;;+2/p-2Key: CITILBVTAYEWKR-NUQVWONBAZ
SMILES
  • .FC(F)(F)S()(=O)=O.FC(F)(F)S()(=O)=O
Properties
Chemical formula C2F6O6S2Zn
Molar mass 363.51 g·mol
Appearance White powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Zinc trifluoromethanesulfonate or zinc triflate is the zinc salt of trifluoromethanesulfonic acid. It is commonly used as a Lewis acid catalyst, e.g. in silylations.

A white powder, zinc triflate is commercially available, though some workers have experienced inconsistent results with zinc triflate from different sources. If desired, it may be prepared from reacting trifluoromethanesulfonic acid with zinc metal in acetonitrile, or with zinc carbonate in methanol:

Zn + 2 HOTf → Zn(OTf)2 + H2
ZnCO3 + 2 HOTf → Zn(OTf)2 + H2O + CO2 (OTf = CF3SO3)

References

  1. H. Jiang & S. Zhu (2005). "Silylation of 1-alkynes with chlorosilanes promoted by Zn(OTf)2: an efficient way to the preparation of alkynylsilanes". Tetrahedron Letters. 46 (3): 517–519. doi:10.1016/j.tetlet.2004.10.175.
  2. R. J. Rahaim & J. T. Shaw (2008). "Zinc-Catalyzed Silylation of Terminal Alkynes". J. Org. Chem. 73 (7): 2912–2915. doi:10.1021/jo702557d. PMID 18331056.
  3. J. E. D. Kirkham, T. D. L. Courtney, V. Lee and J. E. Baldwin (2005). "Asymmetric synthesis of cytotoxic sponge metabolites R-strongylodiols A and B and an analogue". Tetrahedron. 61 (30): 7219–7232. doi:10.1016/j.tet.2005.05.034.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. J. Lombard, S. Romain, S. Dumas, J. Chauvin, M.-N. Collomb, D. Daveloose, A. Deronzier and J.-C. Leprêtre (2005). "Tetranuclear Polypyridyl Complexes of RuII and FeII: Synthesis, Electrochemical, Photophysical and Photochemical Behaviour". European Journal of Inorganic Chemistry. 2005 (16): 3320–3330. doi:10.1002/ejic.200500106.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. E. J. Corey & K. Shimoji (1983). "Magnesium and zinc-catalyzed thioketalization". Tetrahedron Letters. 24 (2): 169–172. doi:10.1016/S0040-4039(00)81357-X.
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