Diphenylphosphine

Diphenylphosphine

Names
IUPAC name diphenylphosphane
Identifiers
CAS Number	829-85-6 Y
3D model (JSmol)	Interactive image
ChemSpider	63209 Y
ECHA InfoCard	100.011.447
InChI InChI=1S/C12H11P/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H Y Key: GPAYUJZHTULNBE-UHFFFAOYSA-N Y InChI=1/C12H11P/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H Key: GPAYUJZHTULNBE-UHFFFAOYAN
SMILES c2c(Pc1ccccc1)cccc2
Properties
Chemical formula	C12H11P
Molar mass	186.19 g/mol
Appearance	colorless liquid
Density	1.07 g/cm3, liquid
Boiling point	280 °C (536 °F; 553 K)
Solubility in water	Insoluble
Hazards
Safety data sheet	External MSDS
R-phrases (outdated)	17-36/37/38
S-phrases (outdated)	26-36
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

Diphenylphosphine, also known as diphenylphosphane, is an organophosphorus compound with the formula (C₆H₅)₂PH. This foul-smelling, colorless liquid is easily oxidized in air. It is a precursor to organophosphorus ligands for use as catalysts.

Diphenylphosphine can be prepared cheaply from triphenylphosphine.

In the laboratory, diphenylphosphine is a common intermediate. It can be deprotonated to give diphenylphosphide derivatives:

The preparation of phosphine ligands, Wittig-Horner reagents, and phosphonium salts are commonly accomplished by alkylating diphenylphosphine. The hydrogen atom connected to phosphorus undergoes Michael-like addition to activated alkenes, providing products with which to produce phosphine ligands such as 1,2-bis(diphenylphosphino)ethane (Ph₂PC₂H₄PPh₂). Diphenylphosphine and especially diphenylphosphide derivatives are nucleophiles, so they add to carbon – heteroatom double bonds. For example, in the presence of concentrated hydrochloric acid at 100 °C, diphenylphosphine adds to the carbon atom in benzaldehyde to give (phenyl-(phenylmethyl)phosphoryl)benzene.

Compared to tertiary phosphines, diphenylphosphine is weakly basic. The pKa of the protonated derivative is 0.03:

Diphenylphosphine readily oxidizes.

An intermediate in this oxidation is diphenylphosphine oxide. The use of the diphenylphosphine–borane complex, Ph₂PH•BH₃ avoids the problem of phosphine oxidation by protecting the phosphine from oxidation and is available through chemical vendors.