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Merck
CN

734527

Tetrakis(pyridine)copper(II) triflate

95%, crystals

Synonym(s):

[Cu(OTf)2(py)4], Cu(pyridine)4(OTf)2, Tetrakis(pyridine)copper(II) bis(trifluoromethanesulfonate)

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About This Item

Empirical Formula (Hill Notation):
C22H20CuF6N4O6S2
CAS Number:
113110-58-0
Molecular Weight:
678.08
MDL number:
MFCD19105629
UNSPSC Code:
12161600
PubChem Substance ID:
329764907
NACRES:
NA.22

Key Documents

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Product Name

Tetrakis(pyridine)copper(II) triflate, 95%

SMILES string

c1ccncc1.c2ccncc2.c3ccncc3.c4ccncc4.FC(F)(F)S(=O)(=O)O[Cu]OS(=O)(=O)C(F)(F)F

InChI

1S/4C5H5N.2CHF3O3S.Cu/c4*1-2-4-6-5-3-1;2*2-1(3,4)8(5,6)7;/h4*1-5H;2*(H,5,6,7);/q;;;;;;+2/p-2

InChI key

DOUMBTAZXRQKGF-UHFFFAOYSA-L

assay

95%

form

crystals

reaction suitability

core: copper, reagent type: catalyst

mp

190-194 °C

storage temp.

−20°C

Quality Level

100

Related Categories

Application

Tetrakis(pyridine)copper(II) triflate [Cu(OTf)2(py)4] is a general copper-based catalyst. It is commonly used to catalyze copper-mediated radiofluorination of arenes and heteroarene. It is also employed in C(sp3)-H functionalization/cyclisation of 2-amino-N,N-dialkylbenzamides to synthesize 2,3-disubstituted-4(3H)-quinazolinones.
Tetrakis(pyridine)copper(II) triflate can be used to catalyze:
  • Intra and intermolecular aziridination of allylic carbamates and styrenes.
  • 18F-fluorination of aryl boronic esters to generate fluroarenes applicable as radiotracers.
  • Nucleophilic radiobromination of aryl borons with a radiobromide ion applicable in the preparation of radiobrominated pharmaceuticals.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX9027
MKCW6087
MKCV5390
MKCR6463
MKCT0330

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A general copper?mediated nucleophilic 18F fluorination of arenes.
Tredwell M, et al.
Angewandte Chemie (Weinheim an der Bergstrasse, Germany), 126(30), 7885-7889 (2014)
Thomas Keller et al.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism, 40(5), 1012-1020 (2019-05-31)
[18F]F-DPA, a novel translocator protein 18 kDa (TSPO)-specific radioligand for imaging neuroinflammation, has to date been synthesized with low to moderate molar activities (Am's). In certain cases, low Am can skew the estimation of specific binding. The high proportion of the
Copper-catalyzed C?H functionalization reactions: Efficient synthesis of heterocycles.
Guo X X, et al.
Chemical Reviews, 115(3), 1622-1651 (2014)
Synthesis of Cu-catalysed quinazolinones using a C sp3?H functionalisation/cyclisation strategy.
Gholap A V, et al.
Organic & Biomolecular Chemistry, 15(34), 7140-7146 (2017)
Pyrazine and pyridine complexes of copper (II) trifluoromethanesulfonate. Crystal structure of tetrakis (pyridine) bis (trifluoromethanesulfonato-O) copper (II) and magnetic exchange in (pyrazine) bis (trifluoromethanesulfonato-O) copper (II).
Haynes J S, et al.
Inorganic Chemistry, 27(7), 1237-1241 (1988)
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