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1,3-Bis(diphenylphosphino)propane

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1,3-Bis(diphenylphosphino)propane
Names
IUPAC name Propane-1,3-diylbis(diphenylphosphane)
Identifiers
CAS Number
3D model (JSmol)
Abbreviations DPPP
ChEMBL
ChemSpider
ECHA InfoCard 100.027.084 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C27H26P2/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,13,22-23H2Key: LVEYOSJUKRVCCF-UHFFFAOYSA-N
  • InChI=1/C27H26P2/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,13,22-23H2Key: LVEYOSJUKRVCCF-UHFFFAOYAP
SMILES
  • P(c1ccccc1)(c2ccccc2)CCCP(c3ccccc3)c4ccccc4
  • c1ccc(cc1)P(CCCP(c2ccccc2)c3ccccc3)c4ccccc4
Properties
Chemical formula C27H26P2
Molar mass 412.453 g·mol
Appearance white solid
Solubility in water chlorocarbons
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

1,3-Bis(diphenylphosphino)propane (dppp) is a diphosphine often found as a ligand in coordination chemistry.

The diphosphine can be prepared by the reaction of lithium diphenylphosphide and 1,3-dichloropropane.

2 Ph2PLi + C3H6Cl2 → Ph2PC3H6PPh2 + 2 LiCl

The diphosphine is a precursor to the complex dichloro(1,3-bis(diphenylphosphino)propane)nickel, which 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. Dppp is also used as a ligand for palladium(II) catalysts to co-polymerize carbon monoxide and ethylene to give polyketones.

References

  1. Kumada, Makota; Tamao, Kohei; Sumitani, Koji (1988). "Phosphine-Nickel Complex Catalyzed Cross-Coupling of Grignard Reagents with Aryl and Alkenyl Halides: 1,2-dibutylbenzene". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 6, p. 407.
  2. Drent, E.; Mul, W. P.; Smaardijk, A. A. (2001). "Polyketones". Encyclopedia Of Polymer Science and Technology. doi:10.1002/0471440264.pst273.
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