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903000

Sigma-Aldrich

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

Synonym(s):

(4,4′-dtbbpy)NiCl2

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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

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

903000-500MG:4548173353937
903000-BULK:
903000-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN3311
SHBL5154
MKCH6491

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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)
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
Martins S Oderinde et al.
The Journal of organic chemistry, 80(15), 7642-7651 (2015-07-04)
In order to achieve reproducibility during iridium-photoredox and nickel dual-catalyzed sp(3)-sp(2) carbon-carbon bond-forming reactions, we investigated the role that molecular oxygen (O2), solvent and light-source (CF lamp or blue LED) play in a variety of Ir-photoredox mediated transformations. The presence
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Nickel-based Catalysts

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

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