Dppe

1,2-Bis(diphenylphosphino)ethane

Names
IUPAC name Ethane-1,2-diylbis(diphenylphosphane)
Other names 1,2-Bis(diphenylphosphino)ethane Diphos Dppe
Identifiers
CAS Number	1663-45-2 Y
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:30669 Y
ChEMBL	ChEMBL68683 Y
ChemSpider	66873 Y
ECHA InfoCard	100.015.246
InChI InChI=1S/C26H24P2/c1-5-13-23(14-6-1)27(24-15-7-2-8-16-24)21-22-28(25-17-9-3-10-18-25)26-19-11-4-12-20-26/h1-20H,21-22H2 Y Key: QFMZQPDHXULLKC-UHFFFAOYSA-N Y InChI=1/C26H24P2/c1-5-13-23(14-6-1)27(24-15-7-2-8-16-24)21-22-28(25-17-9-3-10-18-25)26-19-11-4-12-20-26/h1-20H,21-22H2 Key: QFMZQPDHXULLKC-UHFFFAOYAX
SMILES P(c1ccccc1)(c2ccccc2)CCP(c3ccccc3)c4ccccc4 c1ccc(cc1)P(CCP(c2ccccc2)c3ccccc3)c4ccccc4
Properties
Chemical formula	C26H24P2
Molar mass	398.42 g/mol
Melting point	140 to 142 °C (284 to 288 °F; 413 to 415 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

1,2-Bis(diphenylphosphino)ethane (dppe) is a commonly used bidentate ligand in coordination chemistry. Dppe is almost invariably chelating, although there are examples of monodentate (e.g., W(CO)₅(dppe)) and of bridging behavior.

The preparation of dppe is conducted via the alkylation of NaPPh₂ which is typically prepared from triphenylphosphine (P(C₆H₅)₃) as follows:

P(C₆H₅)₃ + 2 Na → NaP(C₆H₅)₂ + NaC₆H₅

()

NaP(C₆H₅)₂, which is readily air-oxidized, is treated with 1,2-dichloroethane (ClCH₂CH₂Cl) to give dppe:

2 NaP(C₆H₅)₂ + ClCH₂CH₂Cl → (C₆H₅)₂PCH₂CH₂P(C₆H₅)₂ + 2 NaCl

()

The reduction of dppe by lithium to give PhHP(CH₂)₂PHPh has been reported.

Ph₂P(CH₂)₂PPh₂ + 4 Li → PhLiP(CH₂)₂PLiPh + 2 PhLi

()

Hydrolysis by water gives:

PhLiP(CH₂)₂PLiPh + 2 PhLi + 4H₂O → PhHP(CH₂)₂PHPh + 4 LiOH + 2C₆H₆

()

Treatment of dppe with conventional oxidants such as hydrogen peroxide (H₂O₂), aqueous bromine (Br₂), etc., always produces dppeO in low yield (e.g., 13%) as a result of non-selective oxidation leading to mixtures of the starting material, the monoxide, and dioxide. Selective mono-oxidation of dppe can be achieved by reaction with PhCH₂Br to give dppeO.