Bis(triphenylphosphine)nickel(II)chloride
[CAS# 14264-16-5]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic nickel
• Name: Bis(triphenylphosphine)nickel(II)chloride
• Synonyms: Dichlorobis(triphenylphosphine)nickel(II)
• Molecular Formula: C₃₆H₃₀Cl₂NiP₂
• Molecular Weight: 654.18
• CAS Registry Number: 14264-16-5
• EC Number: 238-154-8
• SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ni]Cl

Properties

• Melting point: 250 °C (dec.)
• Water solubility: insoluble

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H302-H317-H350-H412
• Safety Statements: P203-P261-P264-P270-P272-P273-P280-P301+P317-P302+P352-P318-P321-P330-P333+P317-P362+P364-P405

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Carcinogenicity	Carc.	1B	H350
Acute toxicity	Acute Tox.	4	H302
Carcinogenicity	Carc.	1A	H350
Acute toxicity	Acute Tox.	4	H332
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H312
Respiratory sensitization	Resp. Sens.	1	H334

Discovery and Applications

Bis(triphenylphosphine)nickel(II)chloride is a well-known organometallic compound, notable for its utility in various chemical processes due to its unique properties. This complex features a nickel(II) center coordinated by two triphenylphosphine ligands and one chloride ion. Its synthesis and applications span several fields, including catalysis and materials science.

The discovery of Bis(triphenylphosphine)nickel(II)chloride is rooted in the exploration of nickel-based catalysts. Researchers identified the compound as a versatile and stable nickel(II) complex with significant potential in catalysis due to its favorable electronic and steric properties. The triphenylphosphine ligands provide strong coordination to the nickel center, enhancing its stability and reactivity. The chloride ion completes the coordination sphere of the nickel center, contributing to the overall stability of the complex.

In catalysis, Bis(triphenylphosphine)nickel(II)chloride is particularly valued for its role in cross-coupling reactions, such as the Suzuki-Miyaura coupling. This reaction involves the formation of carbon-carbon bonds between an aryl or vinyl halide and an organoboron compound. The nickel(II) center in Bis(triphenylphosphine)nickel(II)chloride acts as the active catalyst, facilitating the coupling process and enabling the formation of various organic products. The choice of triphenylphosphine as a ligand is crucial as it stabilizes the nickel center and helps in the formation of active catalytic species.

Beyond catalysis, Bis(triphenylphosphine)nickel(II)chloride is used in the development of new materials. The compound's ability to form coordination polymers and complexes with other ligands has led to its use in synthesizing materials with tailored properties. These materials are employed in various applications, including electronic devices and sensors, where precise control over material properties is essential.

In addition, the study of Bis(triphenylphosphine)nickel(II)chloride contributes to our understanding of nickel chemistry and its role in coordination complexes. Research on this compound has provided insights into the behavior of nickel(II) complexes in different chemical environments, including their stability, reactivity, and interaction with other ligands.

Overall, Bis(triphenylphosphine)nickel(II)chloride remains a significant compound in both academic research and practical applications. Its role in catalysis, materials science, and fundamental chemistry underscores its importance in advancing our knowledge and technological capabilities.

References

1979. Reactions of Metallacycles of Nickel, Metallacyclopentanes, Hexanes and Butanes. Fundamental Research in Homogeneous Catalysis.
URL: https://doi.org/10.1007/978-1-4613-2958-9_11

2024. Recent Advances in C-O Bond Cleavage of Aryl, Vinyl, and Benzylic Ethers. Topics in current chemistry (Cham).
DOI: https://pubmed.ncbi.nlm.nih.gov/39570456

2019. Advances in Kumada-Tamao-Corriu cross-coupling reaction: an update. Monatshefte für Chemie - Chemical Monthly.
DOI: https://doi.org/10.1007/s00706-019-2364-6