Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

903000

Sigma-Aldrich

[4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine] nickel (II) dichloride

Synonym(s):

(4,4′-dtbbpy)NiCl2

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C18H24Cl2N2Ni
CAS Number:
1034901-50-2
Molecular Weight:
398.00
UNSPSC Code:
12352101
NACRES:
NA.22

form

powder or crystals

reaction suitability

core: nickel
reaction type: Cross Couplings
reagent type: catalyst

mp

>300 °C

SMILES string

CC(C1=CC(C2=CC(C(C)(C)C)=CC=N2)=NC=C1)(C)C.Cl[Ni]Cl

Application

[4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine] nickel (II) dichloride can be used as a catalyst in:
  • Decarboxylative arylation of oxo acids.
  • Acylation of ethers.
  • Cross-coupling of aryl bromides with alcohols.

Other Notes

Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo Acids

Photocatalytic α-Acylation of Ethers

related product

Product No.
Description
Pricing

335363

[1,3-Bis(diphenylphosphino)propane]dichloronickel(II)

728551

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

804398

[(TMEDA)Ni(o-tolyl)Cl], 95%

902993

(BPhen)Ni(OAc)2.xH2O

902985

(Bathocuproine)NiBr2

903019

[4,4′-Dimethyl-2,2′-bipyridine]nickel(II) dichloride hydrate, ≥95%

904937

2,6-Bis(N-pyrazolyl)pyridine nickel (II) dichloride, ≥95% anhydrous basis

907111

2,6-bis(N-pyrazolyl)pyridine nickel(II) bromide

911534

(4,4′-dMeObpy)NiCl2

911844

(Me4Phen)NiCl2

911984

(2,2′-Bipyridine)diiodonickel(II)

913014

[1,3-Bis(diphenylphosphino)propane]dibromonickel(II), ≥95%

913278

[1,2-Bis(diphenylphosphino)ethane]dibromonickel(II), ≥95%

913154

1,10-Phenanthroline nickel (ll) dibromide

916129

1,10-Phenanthroline nickel (ll) dichloride

917982

Tetrapyridyl nickel (ll) dichloride, ≥95%

918083

2,9-Dimethyl-1,10-phenanthroline nickel (ll) bromide

924245

Deoxazole, ≥95%

924253

Deoxazole-quat, ≥95%

Storage Class Code

11 - Combustible Solids

WGK

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Aryl Ketones as Single-Electron-Transfer Photoredox Catalysts in Nickel-Catalyzed the Homocoupling of Aryl Halides
Masuda Y, et al.
European Journal of Organic Chemistry, 5822-5825 (2016)
Photocatalytic α-Acylation of Ethers
Sun Z, et al.
Organic Letters, 19, 3727-3730 (2017)
Wacharee Harnying et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(17), 4765-4773 (2011-03-23)
The roles of nickel and chromium catalysts in the coupling reaction of vinyl halides and aldehydes, the so-called Nozaki-Hiyama-Kishi (NHK) reaction, have been studied by UV/Vis spectroscopy, electrochemical, and spectroelectrochemical methods. Electrochemical studies revealed that nickel plays the central role
Ir III/Ni II-Metallaphotoredox catalysis: the oxidation state modulation mechanism versus the radical mechanism
Zhu B, et al.
Chemical Communications (Cambridge, England), 54, 5968-5971 (2018)
Merging photoredox and nickel catalysis: The direct synthesis of ketones by the decarboxylative arylation of α-oxo acids
Chu L, et al.
Angewandte Chemie (International ed. in English), 127, 8040-8044 (2015)
View All Related Papers

Articles

Nickel-based Catalysts

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

Nickel-based Catalysts

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

Nickel-based Catalysts

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

Nickel-based Catalysts

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service