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1,2-Bis(diphenylphosphino)ethane nickel(II) chloride
[CAS# 14647-23-5]

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Complete supplier list of 1,2-Bis(diphenylphosphino)ethane nickel(II) chloride
Identification
Classification Chemical reagent >> Organic reagent >> Phosphine ligand
Name 1,2-Bis(diphenylphosphino)ethane nickel(II) chloride
Molecular Structure CAS # 14647-23-5, 1,2-Bis(diphenylphosphino)ethane nickel(II) chloride
Molecular Formula C26H24Cl2NiP2
Molecular Weight 528.02
CAS Registry Number 14647-23-5
EC Number 629-489-4
SMILES C1=CC=C(C=C1)P(CCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.[Cl-].[Cl-].[Ni+2]
Properties
Melting point 263-265 ºC
Water solubility insoluble
Safety Data
Hazard Symbols symbol symbol   GHS07;GHS08 Danger    Details
Hazard Statements H302-H312-H315-H317-H319-H332-H334-H335-H350-H351    Details
Precautionary Statements P203-P233-P260-P261-P264-P264+P265-P270-P271-P272-P280-P284-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P318-P319-P321-P330-P332+P317-P333+P317-P337+P317-P342+P316-P362+P364-P403-P403+P233-P405-P501    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Skin irritationSkin Irrit.2H315
Eye irritationEye Irrit.2H319
Respiratory sensitizationResp. Sens.1H334
Acute toxicityAcute Tox.4H332
Acute toxicityAcute Tox.4H312
Acute toxicityAcute Tox.4H302
Specific target organ toxicity - single exposureSTOT SE3H335
CarcinogenicityCarc.1BH350
Skin sensitizationSkin Sens.1H317
CarcinogenicityCarc.1AH350
Reproductive toxicityRepr.1BH360
Acute hazardous to the aquatic environmentAquatic Acute1H400
Specific target organ toxicity - repeated exposureSTOT RE1H372
Acute toxicityAcute Tox.3H331
Chronic hazardous to the aquatic environmentAquatic Chronic1H410
CarcinogenicityCarc.2H351
Acute toxicityAcute Tox.3H301
SDS Available
up Discovory and Applicatios
1,2-Bis(diphenylphosphino)ethane nickel(II) chloride, often referred to as Ni(dppp)Cl₂, is a prominent example of a nickel-based complex with significant applications in organometallic chemistry and catalysis. This compound, featuring a nickel(II) center coordinated by two diphenylphosphine groups and chloride ligands, has been instrumental in advancing various chemical transformations.

The discovery of 1,2-Bis(diphenylphosphino)ethane nickel(II) chloride is rooted in the broader exploration of transition metal complexes for catalytic purposes. The ligand, 1,2-Bis(diphenylphosphino)ethane (dppp), was designed to provide enhanced stability and reactivity to metal centers through its bidentate phosphine functionality. This design allows for effective coordination with the nickel center, leading to the formation of a stable, yet reactive, nickel(II) complex.

This complex has become a valuable tool in a range of catalytic processes. Its primary applications include facilitating cross-coupling reactions, which are fundamental in the synthesis of complex organic molecules. These reactions involve the formation of carbon-carbon bonds and are widely used in pharmaceutical and materials chemistry. Ni(dppp)Cl₂ is particularly noted for its role in Suzuki-Miyaura and Negishi coupling reactions, where it helps in the coupling of aryl and vinyl halides with organoboron or organozinc reagents.

The effectiveness of Ni(dppp)Cl₂ in these reactions is attributed to the electronic and steric properties imparted by the dppp ligand. The phosphine groups provide significant electron-donating effects, which stabilize the nickel center and facilitate its interaction with substrates. The resulting complex can promote reactions with high efficiency, offering a viable alternative to palladium-based catalysts in some cases.

In addition to its role in cross-coupling reactions, 1,2-Bis(diphenylphosphino)ethane nickel(II) chloride has been employed in other types of catalytic transformations, including hydrogenation and polymerization reactions. Its versatility makes it a valuable component in the toolkit of synthetic chemists seeking to explore new reaction pathways or improve existing processes.

The ongoing research into nickel-based catalysts, including Ni(dppp)Cl₂, reflects a broader trend towards developing more cost-effective and environmentally benign alternatives to precious metal catalysts. Nickel, being more abundant and less expensive than palladium or platinum, offers a promising route for sustainable chemistry.

Overall, 1,2-Bis(diphenylphosphino)ethane nickel(II) chloride represents a significant advancement in the field of organometallic chemistry. Its discovery and subsequent applications illustrate the impact of transition metal complexes on modern chemical synthesis, highlighting the importance of innovative ligand design and catalytic optimization.
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