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Copper(II) triflate

Summary

Copper(II) triflate is the copper(II) salt of trifluoromethanesulfonic acid (known simply as triflic acid) which has a chemical formula of Cu(OSO2CF3)2, abbreviated Cu(OTf)2. This substance, first reported in 1972,[2] is a powerful Lewis acid. It is used as a catalyst in several organic reactions, such as the Diels–Alder reaction[3] and cyclopropanation reactions[4] (much like rhodium(II) acetate).

Copper(II) triflate
Copper(II) triflate
Names
IUPAC name
Copper(II) trifluoromethanesulfonate
Other names
Copper(II) triflate
Identifiers
  • 34946-82-2 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 2016731 checkY
ECHA InfoCard 100.047.531 Edit this at Wikidata
  • 2734996
  • DTXSID80894787 Edit this at Wikidata
  • InChI=1S/2CHF3O3S.Cu/c2*2-1(3,4)8(5,6)7;/h2*(H,5,6,7);/q;;+2/p-2 checkY
    Key: SBTSVTLGWRLWOD-UHFFFAOYSA-L checkY
  • InChI=1/2CHF3O3S.Cu/c2*2-1(3,4)8(5,6)7;/h2*(H,5,6,7);/q;;+2/p-2
    Key: SBTSVTLGWRLWOD-NUQVWONBAL
  • [Cu+2].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O
Properties
C2CuF6O6S2
Molar mass 361.67 g·mol−1
Appearance white to pale blue powder
very soluble, hygroscopic
Hazards
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 1 mg/m3 (as Cu)[1]
REL (Recommended)
 TWA 1 mg/m3 (as Cu)[1]
IDLH (Immediate danger)
 TWA 100 mg/m3 (as Cu)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References edit

  1. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0150". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ Jenkins, C.L.; Kochi, J.K. (1972). "Solvolytic Routes via Alkylcopper Intermediates in the Electron-Transfer Oxidation of Alkyl Radicals". Journal of the American Chemical Society. 94 (3): 843–855. doi:10.1021/ja00758a024.
  3. ^ Evans, D.A.; Miller, S.J.; Lectka, T.; von Matt, P. (1999). "Chiral Bis(oxazoline)copper(II) Complexes as Lewis Acid Catalysts for the Enantioselective Diels–Alder Reaction". Journal of the American Chemical Society. 121 (33): 7559–7573. doi:10.1021/ja991190k.
  4. ^ Salomon, R.G.; Kochi, J.K (1973). "Copper(I) catalysis in cyclopropanations with diazo compounds. Role of olefin coordination". Journal of the American Chemical Society. 95 (10): 3300–3310. doi:10.1021/ja00791a038.