Names | |
---|---|
Preferred IUPAC name
(Propane-1,3-diyl)bis(diphenylphosphane) | |
Identifiers | |
3D model (
JSmol)
|
|
Abbreviations | DPPP |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.027.084 |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C27H26P2 | |
Molar mass | 412.453 g·mol−1 |
Appearance | white solid |
chlorocarbons | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
1,3-Bis(diphenylphosphino)propane (dppp) is an organophosphorus compound with the formula Ph2P(CH2)3PPh2. The compound is a white solid that is soluble in organic solvents. It is slightly air-sensitive, degrading in air to the phosphine oxide. It is classified as a diphosphine ligand in coordination chemistry and homogeneous catalysis.
The diphosphine can be prepared by the reaction of lithium diphenylphosphide and 1,3-dichloropropane (Ph = C6H5):
However, it can be synthesised via a much more controllable (and cheaper) route, via metal-halogen exchange and then metathesis:
The diphosphine serves as a bidentate ligand forming six-membered C3P2M chelate ring with a natural bite angle of 91°. [1] For example, the complex dichloro(1,3-bis(diphenylphosphino)propane)nickel is prepared by combining equimolar portions of the ligand and nickel(II) chloride hexahydrate. This nickel complex serves as a catalyst for the Kumada coupling reaction. [2] Dppp is also used as a ligand for palladium(II) catalysts to co-polymerize carbon monoxide and ethylene to give polyketones. [3] Dppp can sometimes be used in palladium-catalyzed arylation under Heck reaction conditions to control regioselectivity. [4]
Names | |
---|---|
Preferred IUPAC name
(Propane-1,3-diyl)bis(diphenylphosphane) | |
Identifiers | |
3D model (
JSmol)
|
|
Abbreviations | DPPP |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.027.084 |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C27H26P2 | |
Molar mass | 412.453 g·mol−1 |
Appearance | white solid |
chlorocarbons | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
1,3-Bis(diphenylphosphino)propane (dppp) is an organophosphorus compound with the formula Ph2P(CH2)3PPh2. The compound is a white solid that is soluble in organic solvents. It is slightly air-sensitive, degrading in air to the phosphine oxide. It is classified as a diphosphine ligand in coordination chemistry and homogeneous catalysis.
The diphosphine can be prepared by the reaction of lithium diphenylphosphide and 1,3-dichloropropane (Ph = C6H5):
However, it can be synthesised via a much more controllable (and cheaper) route, via metal-halogen exchange and then metathesis:
The diphosphine serves as a bidentate ligand forming six-membered C3P2M chelate ring with a natural bite angle of 91°. [1] For example, the complex dichloro(1,3-bis(diphenylphosphino)propane)nickel is prepared by combining equimolar portions of the ligand and nickel(II) chloride hexahydrate. This nickel complex serves as a catalyst for the Kumada coupling reaction. [2] Dppp is also used as a ligand for palladium(II) catalysts to co-polymerize carbon monoxide and ethylene to give polyketones. [3] Dppp can sometimes be used in palladium-catalyzed arylation under Heck reaction conditions to control regioselectivity. [4]