[4,4'-Bis(1,1-dimethylethyl)-2,2'-bipyridine] nickel (II) dichloride
[CAS# 1034901-50-2]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic nickel
• Name: [4,4'-Bis(1,1-dimethylethyl)-2,2'-bipyridine] nickel (II) dichloride
• Synonyms: dichloronickel
• Molecular Formula: C₁₈H₂₄Cl₂N₂Ni
• Molecular Weight: 398.00
• CAS Registry Number: 1034901-50-2
• EC Number: 876-244-4
• SMILES: CC(C)(C)C1=CC(=NC=C1)C2=NC=CC(=C2)C(C)(C)C.Cl[Ni]Cl

Properties

• Melting point: >300 ºC

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Danger
• Hazard Statements: H302-H319-H372-H410
• Precautionary Statements: P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Germ cell mutagenicity	Muta.	2	H341
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317
Respiratory sensitization	Resp. Sens.	1	H334
Skin irritation	Skin Irrit.	2	H315
Reproductive toxicity	Repr.	2	H361
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Carcinogenicity	Carc.	2	H351

Discovory and Applicatios

[4,4'-Bis(1,1-dimethylethyl)-2,2'-bipyridine] nickel(II) dichloride is an organometallic complex that has attracted interest for its potential applications in catalysis, particularly in cross-coupling reactions. This nickel(II) complex features a bipyridine ligand substituted with tert-butyl groups, which enhances its stability and catalytic efficiency.

The discovery of this complex stems from the need for cost-effective alternatives to palladium-based catalysts, which are commonly used in cross-coupling reactions. Nickel, being less expensive and more abundant than palladium, offers an attractive alternative. The incorporation of the 4,4'-bis(1,1-dimethylethyl)-2,2'-bipyridine ligand into the nickel complex enhances the catalyst's performance by providing steric hindrance and electronic properties that favor the desired catalytic activity.

[4,4'-Bis(1,1-dimethylethyl)-2,2'-bipyridine] nickel(II) dichloride has proven to be effective in a variety of cross-coupling reactions, including Suzuki-Miyaura, Kumada, and Negishi couplings. These reactions are fundamental in organic synthesis, allowing the formation of carbon-carbon bonds, which are essential for constructing complex molecules such as pharmaceuticals, agrochemicals, and advanced materials.

In Suzuki-Miyaura coupling, the nickel complex facilitates the reaction between aryl halides and boronic acids, producing biaryl compounds with high efficiency. Similarly, in Kumada coupling, it enables the cross-coupling of aryl or vinyl halides with Grignard reagents. The versatility of this nickel catalyst is further demonstrated in Negishi coupling, where it mediates the reaction between organozinc reagents and halides.

The ability of [4,4'-Bis(1,1-dimethylethyl)-2,2'-bipyridine] nickel(II) dichloride to catalyze these reactions with high selectivity and under mild conditions has made it a valuable tool in synthetic chemistry. Its effectiveness in promoting cross-coupling reactions has spurred interest in its use for the synthesis of complex organic molecules, offering a cost-effective and efficient alternative to traditional palladium-based catalysts.

In summary, [4,4'-Bis(1,1-dimethylethyl)-2,2'-bipyridine] nickel(II) dichloride is a promising nickel-based catalyst that has expanded the possibilities in cross-coupling chemistry, providing a reliable and economical option for various synthetic applications.