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762504

Sigma-Aldrich

Bis[(tetrabutylammonium iodide)copper(I) iodide]

95%

Synonym(s):

Tetrabutylammonium iodide copper(I) iodide dimer

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About This Item

Empirical Formula (Hill Notation):
C32H72Cu2I4N2
Molecular Weight:
1119.64
MDL number:
MFCD22200557
UNSPSC Code:
12161600
PubChem Substance ID:
329766980
NACRES:
NA.22

assay

95%

form

solid

reaction suitability

core: copper
reagent type: catalyst

mp

90-97 °C

SMILES string

[I-].[I-].[Cu]I.[Cu]I.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC

InChI

1S/2C16H36N.2Cu.4HI/c2*1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;;;;;;/h2*5-16H2,1-4H3;;;4*1H/q4*+1;;;;/p-4

InChI key

AVVGGLORWAVEFH-UHFFFAOYSA-J

Related Categories

Application

Bis[(tetrabutylammonium iodide)copper(I) iodide] can be used as a catalyst:
  • To synthesize 1,4-disubstituted 1,2,3-triazoles via three-component click reaction.
  • For the N-arylation of indoles in the presence of potassium carbonate as a base.
  • In the Ullmann coupling reaction in the presence of cesium carbonate and acetonitrile.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A soluble copper (I) source and stable salts of volatile ligands for copper-catalyzed C-X couplings
Maligres P, et al.
The Journal of Organic Chemistry, 77 (2012)
Carmela Molinaro et al.
The Journal of organic chemistry, 84(12), 8006-8018 (2019-05-28)
A practical and efficient enantioselective synthesis of the calcitonin gene-related peptide receptor antagonist 1 has been developed. The key structural component of the active pharmaceutical ingredient is a syn-1,2-amino-fluoropiperidine 4. Two approaches were developed to synthesize this important pharmacophore. Initially
A recyclable and water soluble copper (I)-catalyst: one-pot synthesis of 1, 4-disubstituted 1, 2, 3-triazoles and their biological evaluation
Nekkanti S, et al
Royal Society of Chemistry Advances, 6, 103556-103566 (2016)

Protocols

KitAlysis™ High-Throughput Copper C-N Cross-Coupling Reaction Screening Kit

KitAlysis™ Cu C-N (Buchwald-Hartwig) cross-coupling high-throughput screening kit. Detailed Set-Up User Guide and a downloadable excel file for calculations.

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