1,3-Bis(diphenylphosphino)propane

Names
Preferred IUPAC name

(Propane-1,3-diyl)bis(diphenylphosphane)

Identifiers

CAS Number

* 6737-42-4 Y

3D model (JSmol)

* Interactive image
* Interactive image

Abbreviations  | DPPP
ChEMBL |

* ChEMBL73394 Y

ChemSpider |

* 73276 Y

PubChem CID

* 81219

UNII |

* 44R56E2C68 Y

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

SMILES

* P(c1ccccc1)(c2ccccc2)CCCP(c3ccccc3)c4ccccc4

* c1ccc(cc1)P(CCCP(c2ccccc2)c3ccccc3)c4ccccc4

Properties

Chemical formula

| C27H26P2
Molar mass | 412.453 g·mol−1
Appearance  | white solid

Solubility in water

| chlorocarbons

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

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):

2 Ph2PLi + Cl(CH2)3Cl → Ph2P(CH2)3PPh2 \+ 2 LiCl

However, it can be synthesised via a much more controllable (and cheaper) route, via metal-halogen exchange and then metathesis:

Br(CH2)3Br + 2 tBuLi → Li(CH2)3Li + 2 tBuBr
Li(CH2)3Li + 2 PCl3 → Cl2P(CH2)3PCl2 \+ 2 LiCl
Cl2P(CH2)3PCl2 \+ 4 PhLi → Ph2P(CH2)3PPh2 \+ 4 LiCl

## Coordination chemistry and use as co-catalyst

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]

## References

1. ↑ Birkholz (née Gensow), Mandy-Nicole; Freixa, Zoraida; van Leeuwen, Piet W. N. M. (2009). "Bite angle effects of diphosphines in C–C and C–X bond forming cross coupling reactions". Chemical Society Reviews 38 (4): 1099–1118. doi:10.1039/B806211K. PMID 19421583.
2. ↑ 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. http://www.orgsyn.org/demo.aspx?prep=cv6p0407. ;  Collective Volume, 6, pp. 407
3. ↑ Drent, E.; Mul, W. P.; Smaardijk, A. A. (2001). "Polyketones". Encyclopedia Of Polymer Science and Technology. doi:10.1002/0471440264.pst273. ISBN 9781118633892.
4. ↑ Cabri, Walter; Candiani, Ilaria; Bedeschi Angelo; Penco, Sergio"α-Regioselectivity in Palladium-Catalyzed Arylation of Acyclic Enol Ethers" journal= Journal of Organic Chemistry, 1991, volume 57, p. 1481. doi:10.1021/jo00031a029

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*[CID]: Compound ID