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Chemical compound From Wikipedia, the free encyclopedia
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.
Names | |
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Systematic IUPAC name
Dichloro[1,3-propanediylbis(diphenylphosphanuide-κP)]nickel | |
Other names
1,3-bis(diphenylphosphino)propanenickel(II) chloride | |
Identifiers | |
3D model (JSmol) |
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ChemSpider | |
ECHA InfoCard | 100.132.628 |
EC Number |
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PubChem CID |
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CompTox Dashboard (EPA) |
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Properties | |
C27H26Cl2NiP2 | |
Molar mass | 542.05 g·mol−1 |
Appearance | Orange to red-orange powder |
Melting point | 213 °C (415 °F; 486 K) |
Insoluble | |
Hazards | |
GHS labelling: | |
[1] | |
Danger[1] | |
H315, H317, H319, H334, H335, H350[1] | |
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).
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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]
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]
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