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Copper(II) trifluoromethanesulfonate

Catalog Number
ACM34946822
Product Name
Copper(II) trifluoromethanesulfonate
CAS
34946-82-2
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Synonyms
Copper(II) triflate
IUPAC Name
copper;trifluoromethanesulfonate;
Molecular Weight
361.7
Molecular Formula
C2CuF6O6S2
Canonical SMILES
C(F)(F)(F)S(=O)(=O)[O-].C(F)(F)(F)S(=O)(=O)[O-].[Cu+2]
InChI
InChI=1S/2CHF3O3S.Cu/c2*2-1(3,4)8(5,6)7;/h2*(H,5,6,7);/q;+2/p-2
InChI Key
SBTSVTLGWRLWOD-UHFFFAOYSA-L
Melting Point
≥300 °C
Purity
99%+
Appearance
Powder
Complexity
145
Covalently-Bonded Unit Count
3
EC Number
252-300-8
Exact Mass
360.833646
H-Bond Acceptor
12
Heavy Atom Count
17
Monoisotopic Mass
360.833646
Rotatable Bond Count
0
Topological Polar Surface Area
131 Ų
Application
Copper(II) trifluoromethanesulfonate serves as a versatile mild Lewis acid, primarily functioning as a catalyst in various organic transformations. It efficiently facilitates the dehydration of alcohols and diols to alkenes at ambient temperatures. The compound is instrumental in generating carbenoid species from α-diazocarbonyl compounds via in situ reduction, enabling the formation of aziridines from diazo esters and imines. Its catalytic prowess extends to syn-selective aldol condensations, Friedel-Crafts alkylation and acylation reactions of aromatics, and the addition of trimethylsilyl cyanide to carbonyl compounds. Moreover, it plays a crucial role in the ring-opening of epoxides and aziridines. The product finds applications in asymmetric conjugate additions, aziridination, cycloadditions, and Kharasch oxidations, demonstrating its capability in enantioselective transformations like intramolecular aminooxygenations and the addition of organozinc reagents. It also facilitates Pd-catalyzed C-H functionalizations, diacetoxylation of olefins, and the direct arylation of α-aryl carbonyl compounds. Additionally, Copper(II) trifluoromethanesulfonate is employed in Nazarov cyclizations and the three-component coupling of amines, aldehydes, and alkynes, underscoring its broad applicability in synthetic chemistry.
January 4, 2025

Essential Catalyst for Advanced Organic Synthesis

Copper(II) trifluoromethanesulfonate is a transformative catalyst in my research. It efficiently facilitated dehydration of alcohols and supported complex aldol condensations seamlessly, enhancing reaction specificity. Its reliability and versatility are unmatched. Highly recommended for advanced synthesis.

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