Dichloro[1,3-bis(diphenyl­phosphino)propane]nickel

Names
Systematic IUPAC name Dichloro[1,3-propanediylbis(diphenylphosphanuide-κP)]nickel
Other names 1,3-bis(diphenyl­phosphino)propanenickel(II) chloride; NiCl2(dppp)
Identifiers
CAS Number	15629-92-2 Y
3D model (JSmol)	Interactive image
ChemSpider	2007051 N
ECHA InfoCard	100.132.628
EC Number	605-052-3
PubChem CID	6329934
CompTox Dashboard (EPA)	DTXSID50935419
InChI InChI=1S/C27H26P2.2Cl.Ni/c1-5-14-24(15-6-1)28(25-16-7-2-8-17-25)22-13-23-29(26-18-9-3-10-19-26)27-20-11-4-12-21-27;;;/h1-12,14-21H,13,22-23H2;;;
SMILES Cl[Ni]1([P](c2ccccc2)(c3ccccc3)CCC[P]1(c4ccccc4)c5ccccc5)Cl
Properties
Chemical formula	C27H26Cl2NiP2
Molar mass	542.05 g·mol−1
Appearance	Orange to red-orange powder
Melting point	213 °C (415 °F; 486 K)
Solubility in water	Insoluble
Hazards
GHS labelling:
Pictograms	[1]
Signal word	Danger[1]
Hazard statements	H315, H317, H319, H334, H335, H350[1]
Precautionary statements	P201, P261, P280, P305+P351+P338, P308+P313[1]
Safety data sheet (SDS)	External SDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Dichloro[1,3-bis(diphenylphosphino)propane]nickel a coordination complex with the formula NiCl₂(dppp); where dppp is the diphosphine 1,3-bis(diphenylphosphino)propane. It is used as a catalyst in organic synthesis. The compound is a bright orange-red crystalline powder.

While the electronic and solid-state structure of the chloride congener is not known (due to low solubility in common analytical solvents), several studies have been carried out on the bromo and iodo derivatives.^[2] The complexes display a temperature-dependent interconversion between square-planar and tetrahedral geometries (diamagnetic and paramagnetic) in polar organic solvents (Keq between 1-3.68, depending on the solvent and temperature). In contrast, dichloro(1,2-bis(diphenylphosphino)ethane)nickel adopts a static square-planar (diamagnetic) structure in solution.

NiCl₂(dppp) is prepared by combining equal molar portions of nickel(II) chloride hexahydrate with 1,3-bis(diphenylphosphino)propane in 2-propanol.^[3]

Ni(H₂O)₆Cl₂ + dppp → NiCl₂(dppp) + 6 H₂O

NiCl₂(dppp) in an effective catalyst for coupling reactions such as the Kumada coupling^[3] and Suzuki reactions (example below).^[4] It also catalyzes other reactions that convert enol ethers, dithioacetals, and vinyl sulfides to olefins.^[5][6]