[1,3-Bis(diphenylphosphino)propane]nickel(II) chloride
[CAS# 15629-92-2]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic nickel
• Name: [1,3-Bis(diphenylphosphino)propane]nickel(II) chloride
• Molecular Formula: C₂₇H₂₆Cl₂NiP₂
• Molecular Weight: 542.05
• CAS Registry Number: 15629-92-2
• EC Number: 605-052-3
• SMILES: C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.Cl[Ni]Cl

Properties

• Melting point: 213 °C
• Water solubility: insoluble

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H315-H317-H319-H334-H335-H350
• Safety Statements: P203-P233-P260-P261-P264-P264+P265-P271-P272-P280-P284-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P332+P317-P333+P317-P337+P317-P342+P316-P362+P364-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Carcinogenicity	Carc.	1A	H350
Skin sensitization	Skin Sens.	1	H317
Respiratory sensitization	Resp. Sens.	1	H334
Carcinogenicity	Carc.	2	H351
Specific target organ toxicity - single exposure	STOT SE	2	H371
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	3	H301

Discovery and Applications

[1,3-Bis(diphenylphosphino)propane]nickel(II) chloride, commonly referred to as Ni(dppp)Cl₂, is a significant compound in coordination chemistry and catalysis. This chemical substance features a nickel center coordinated to a bidentate diphosphine ligand, 1,3-bis(diphenylphosphino)propane, and two chloride ions. The discovery and applications of Ni(dppp)Cl₂ highlight its importance in various catalytic processes.

The compound was first synthesized in the early 1970s as part of efforts to explore new nickel-based catalysts for organic transformations. The use of diphosphine ligands, such as dppp, allows for the stabilization of the nickel center and the formation of various nickel complexes. The dppp ligand is particularly valuable due to its bidentate nature, which provides a chelating effect that enhances the stability of the metal complex.

Ni(dppp)Cl₂ has gained prominence for its role in catalyzing a range of important chemical reactions. One of its primary applications is in the hydrocyanation of alkenes, where it serves as a catalyst for the addition of hydrogen cyanide to olefins, producing nitriles. This reaction is useful in the synthesis of valuable intermediates and fine chemicals.

Another notable application of Ni(dppp)Cl₂ is in the hydrogenation of olefins. In this process, the nickel complex facilitates the addition of hydrogen to double bonds, converting alkenes to alkanes. This reaction is crucial in the petrochemical industry for the production of various saturated hydrocarbons and in the synthesis of pharmaceuticals and other organic compounds.

Additionally, Ni(dppp)Cl₂ is employed in the coupling reactions, such as the Negishi coupling, where it participates in the formation of carbon-carbon bonds between organohalides and organozinc reagents. This application is significant for constructing complex organic molecules with precision and efficiency.

The discovery of [1,3-Bis(diphenylphosphino)propane]nickel(II) chloride and its subsequent applications underscore the importance of nickel-based catalysts in modern chemistry. Its ability to facilitate diverse chemical reactions makes it a versatile and valuable tool in both academic research and industrial processes. The development of Ni(dppp)Cl₂ has contributed to advancements in synthetic chemistry by providing a robust and efficient means for achieving various chemical transformations.

References

2024-06-17. Controlled synthesis and optical investigation of conjugated rod-coil diblock copolymer based on poly(3-hexylthiophene) and poly(2-(dimethylamino)ethyl methacrylate-random-1-pyrenylmethyl methacrylate-random-methacrylate spirooxazine).
DOI: 10.1007/s13233-024-00285-3

2024-04-08. New pyrazine-based π-conjugated polymer for dopant-free perovskite solar cell.
DOI: 10.1007/s13233-023-00243-5

2024-04. Effect of Molecular Weight on Thermoelectric Performance of P3HT Analogues with 2-Propoxyethyl Side Chains.
DOI: 10.1007/s11595-024-2880-z