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Sigma-Aldrich

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

≥97% (AT)

Synonym(s):

Chloro[N2-[2-(dimethylamino-κN)phenyl]-N1,N1-dimethyl-1,2-benzenediaminato-κN1,κN2]-nickel, Nickamine

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About This Item

Empirical Formula (Hill Notation):
C16H20ClN3Ni
CAS Number:
1033772-47-2
Molecular Weight:
348.50
MDL number:
MFCD17015253
UNSPSC Code:
12161600
PubChem Substance ID:
329764408
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.

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Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC3865V
BGBC2394V
BCBK9201V
BCBJ6679V
BCBJ4061V

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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.

Articles

Nickel and Nickel-based Compounds (Complexes) as a Catalyst

Nickel transition metal and its complexes can be used as a catalyst in many synthetic transformations, like oxidative addition, C-H activation, reductive elimination, oxidative cyclization, oligomerization, and in cross-coupling reactions.

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