Tetrakis(triphenylphosphine)nickel
[CAS# 15133-82-1]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic nickel
• Name: Tetrakis(triphenylphosphine)nickel
• Synonyms: Nickel-tetrakis(triphenylphosphine)
• Molecular Formula: 4(C₁₈H₁₅P).Ni
• Molecular Weight: 1107.84
• CAS Registry Number: 15133-82-1
• EC Number: 626-363-0
• 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.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.[Ni]

Properties

• Melting point: 123-128 °C

Safety Data

• Hazard Symbols: GHS02;GHS07;GHS08 Danger
• Risk Statements: H228-H317-H351
• Safety Statements: P203-P210-P240-P241-P261-P272-P280-P302+P352-P318-P321-P333+P317-P362+P364-P370+P378-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Carcinogenicity	Carc.	2	H351
Skin sensitization	Skin Sens.	1	H317
Flammable solids	Flam. Sol.	1	H228

• Transport Information: UN 1325

Discovery and Applications

Tetrakis(triphenylphosphine)nickel is a coordination complex with the formula Ni(PPh3)4, where PPh3 denotes triphenylphosphine. This compound features a nickel center coordinated by four triphenylphosphine ligands. It was first synthesized in the mid-20th century as part of ongoing research into metal-organic complexes and their applications in catalysis.

The discovery of tetrakis(triphenylphosphine)nickel emerged from studies exploring the coordination chemistry of transition metals. The synthesis involves reacting nickel(0) with excess triphenylphosphine in an inert atmosphere. The resulting complex is a robust and stable compound, showcasing the ability of triphenylphosphine to stabilize metal centers and influence their reactivity.

In terms of applications, tetrakis(triphenylphosphine)nickel is predominantly utilized as a catalyst in various organic transformations. Its stability and ability to activate certain chemical bonds make it a valuable tool in synthetic chemistry. One of its significant roles is in facilitating cross-coupling reactions, which are essential for the formation of carbon-carbon bonds. This application is particularly relevant in the synthesis of complex organic molecules and pharmaceuticals.

Additionally, tetrakis(triphenylphosphine)nickel has been employed in studies of catalytic mechanisms and the development of new catalytic processes. Its use extends to the production of fine chemicals, agrochemicals, and materials science, where it helps in creating specialized compounds and materials.

The compound also serves as a model system for understanding the interaction between transition metals and phosphine ligands. Researchers investigate its behavior to gain insights into the electronic and steric effects of the ligands on the metal center, which can be applied to design new catalysts with improved efficiency and selectivity.

Overall, tetrakis(triphenylphosphine)nickel represents an important advancement in coordination chemistry and catalysis. Its discovery has paved the way for significant developments in organic synthesis and the broader field of metal-organic chemistry.

References

2014. Fluorinated Thiophenes and Their Analogues. Fluorine in Heterocyclic Chemistry Volume 1, .
DOI: 10.1007/978-3-319-04346-3_6

2003. Reactions of Aluminium Tribromide with Tetrakis(triphenylphosphine)nickel(0) and Tetrakis(triethylphosphite)nickel(0) Complexes. Russian Journal of Coordination Chemistry, 29(6).
DOI: 10.1023/a:1024042429252

1975. Carbonylation Reactions of Organic Halides by Tetrakis(Triphenylphosphine)Nickel (O) and Palladium (O) Carbonyl Complexes under Mild Conditions. Organotransition-Metal Chemistry, .
DOI: 10.1007/978-1-4684-2142-2_24