Triphenylphosphine

Triphenylphosphine

Names
IUPAC name Triphenylphosphane
Identifiers
CAS Number	603-35-0 Y
3D model (Jmol)	Interactive image
ChemSpider	11283 Y
ECHA InfoCard	100.009.124
EC Number	210-036-0
PubChem	11776
RTECS number	SZ3500000
InChI InChI=1S/C18H15P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H Y Key: RIOQSEWOXXDEQQ-UHFFFAOYSA-N Y InChI=1/C18H15P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H Key: RIOQSEWOXXDEQQ-UHFFFAOYAH
SMILES c3c(P(c1ccccc1)c2ccccc2)cccc3
Properties
Chemical formula	C18H15P
Molar mass	262.29 g·mol−1
Appearance	White Solid
Density	1.1 g cm−3, solid
Melting point	80 °C (176 °F; 353 K)
Boiling point	377 °C (711 °F; 650 K)
Solubility in water	Insoluble
Solubility	organic solvents
Acidity (pKa)	7.61 (pKa of conjugate acid in acetonitrile)
Magnetic susceptibility (χ)	-166.8·10−6 cm3/mol
Refractive index (nD)	1.59; εr, etc.
Structure
Molecular shape	Pyramidal
Dipole moment	1.4 - 1.44 D
Hazards
Safety data sheet	JT Baker
EU classification (DSD)	Not Listed
R-phrases	R20 R22 R40 R43 R50 R53
S-phrases	S36 S37 S45 S57 S60
Flash point	180 °C (356 °F; 453 K)
Related compounds
Related tertiary phosphines	Trimethylphosphine Phosphine
Related compounds	Triphenylamine Triphenylarsine Triphenylphosphine oxide Triphenylphosphine sulfide Triphenylphosphine dichloride Triphenylphosphine selenide, Pd(PPh3)4
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

Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C₆H₅)₃ - often abbreviated to PPh₃ or Ph₃P. It is widely used in the synthesis of organic and organometallic compounds. PPh₃ exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.

Triphenylphosphine is a relatively inexpensive substance. It can be prepared in the laboratory by treatment of phosphorus trichloride with phenylmagnesium bromide or phenyllithium. The industrial synthesis involves the reaction between phosphorus trichloride, chlorobenzene, and sodium.:

Triphenylphosphine undergoes slow oxidation by air to give triphenylphosphine oxide, Ph₃PO:

This impurity can be removed by recrystallisation of PPh₃ from either hot ethanol or hot isopropanol. This method capitalizes on the fact that OPPh₃ is more polar and hence more soluble in polar solvents than PPh₃.

Triphenylphosphine abstracts sulfur from polysulfide compounds, episulfides, and elemental sulfur. Simple organosulfur compounds such as thiols and thioethers are unreactive, however. The phosphorus-containing product is triphenylphosphine sulfide, Ph₃PS. This reaction can be employed to assay the "labile" S⁰ content of a sample, say vulcanized rubber. Triphenylphosphine selenide, Ph₃PSe, may be easily prepared via treatment of PPh₃ with red (alpha-monoclinic) Se. Salts of selenocyanate, SeCN⁻, are used as the Se⁰ source. PPh₃ can also form an adduct with Te, although this adduct primarily exists as (Ph₃P)₂Te rather than PPh₃Te.