1,3-Bis(diphenylphosphino)propane

1,3-Bis(diphenylphosphino)propane
IUPAC name Propane-1,3-diylbis(diphenylphosphane)
Identifiers
Abbreviations	DPPP
CAS number	6737-42-4 Y
PubChem	81219
ChemSpider	73276 Y
ChEMBL	CHEMBL73394 N
Jmol-3D images	Image 1 Image 2
SMILES P(c1ccccc1)(c2ccccc2)CCCP(c3ccccc3)c4ccccc4 c1ccc(cc1)P(CCCP(c2ccccc2)c3ccccc3)c4ccccc4
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,13,22-23H2 Y Key: LVEYOSJUKRVCCF-UHFFFAOYSA-N Y 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,13,22-23H2 Key: LVEYOSJUKRVCCF-UHFFFAOYAP
Properties
Molecular formula	C27H26P2
Molar mass	412.44 g mol−1
Appearance	white solid
Solubility in water	chlorocarbons
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.^[1] Dppp is also used as a ligand for palladium(II) catalysts to co-polymerize carbon monoxide and ethylene to give polyketones.^[2]

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", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p0407 ; Coll. Vol. 6: 407 
2. ^ Drent, E.; Mul, W. P.; Smaardijk, A. A. (2001). "Polyketones". Encyclopedia Of Polymer Science and Technology. doi:10.1002/0471440264.pst273.