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Merck
CN

728551

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

≥97% (AT), lumps

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
UNSPSC Code:
12161600
PubChem Substance ID:
329764408
NACRES:
NA.22
MDL number:
MFCD17015253

Key Documents

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Product Name

Bis[(2-dimethylamino)phenyl]amine nickel(II) chloride, ≥97% (AT)

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

assay

≥97% (AT)

form

lumps

reaction suitability

core: nickel
reagent type: catalyst

Quality Level

200

Related Categories

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000290490
0000239782
0000239782
0000290490
0000204093

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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-based Catalysts

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

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