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Merck

728551

Sigma-Aldrich

Bis[(2-dimethylamino)phenyl]amine nickel(II) chloride

≥97% (AT)

Sinónimos:

Chloro[N2-[2-(dimethylamino-κN)phenyl]-N1,N1-dimethyl-1,2-benzenediaminato-κN1N2]-nickel, Nickamine

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About This Item

Fórmula empírica (notación de Hill):
C16H20ClN3Ni
Número de CAS:
Peso molecular:
348.50
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

assay

≥97% (AT)

form

lumps

reaction suitability

core: nickel
reagent type: catalyst

SMILES string

CN(C)c1ccccc1N([Ni]Cl)c2ccccc2N(C)C

InChI

1S/C16H20N3.ClH.Ni/c1-18(2)15-11-7-5-9-13(15)17-14-10-6-8-12-16(14)19(3)4;;/h5-12H,1-4H3;1H;/q-1;;+2/p-1

InChI key

IRLHVNUEEKJBEL-UHFFFAOYSA-M

Application

Catalyst for:
  • Alkyl-alkyl Kumada coupling of secondary alkyl halides
  • Direct alkylation of heterocyclic C-H bonds
  • Sonogashira coupling of nonactivated alkyl halides
  • Kumada-Corriu-Tamao coupling of nonactivated alkyl halides with aryl and heteroaryl nucleophiles

Reactant of pincer NN2 ligand leading to selective carbon-carbon bond formation

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Related product

Referencia del producto
Descripción
Precios

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificados de análisis (COA)

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Visite la Librería de documentos

Oleg Vechorkin et al.
Angewandte Chemie (International ed. in English), 48(16), 2937-2940 (2009-01-29)
Reacting in the 'Ni'ck of time: The title reaction is realized by using an isolated Ni(II) complex (1). The catalysis tolerates a wide range of important functional groups that are often incompatible with Grignard reagents in cross-coupling reactions.
Zsolt Csok et al.
Journal of the American Chemical Society, 130(26), 8156-8157 (2008-06-06)
A new pincer-type bis(amino)amine (NN2) ligand and its lithium and nickel complexes, including Ni(II) methyl, ethyl, and phenyl complexes, were synthesized. The Ni(II) alkyl complexes react cleanly with alkyl halides including chlorides to form C-C coupled products and Ni(II) halides.

Artículos

Nickel complexes catalyze various synthetic reactions like oxidative addition, C-H activation, and cross-coupling.

Nickel complexes catalyze various synthetic reactions like oxidative addition, C-H activation, and cross-coupling.

Nickel complexes catalyze various synthetic reactions like oxidative addition, C-H activation, and cross-coupling.

Nickel complexes catalyze various synthetic reactions like oxidative addition, C-H activation, and cross-coupling.

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