Triphenylphosphine phenylimide

Triphenylphosphine phenylimide is the organophosphorus compound with the formula Ph₃P=NPh (Ph = C₆H₅). The compound is classified as a phosphanimine. This white solid is soluble in organic solvents. The compound is a prototype of a large class of Staudinger reagents, resulting from the Staudinger reaction.

Triphenylphosphine phenylimide

Names
Preferred IUPAC name Tetraphenylphosphanimine
Other names Tetraphenylphosphine imide N-(Triphenylphosphoranylidene)benzenamine (Phenylimino)triphenylphosphorane N-(Triphenylphosphoranylidene)aniline N-Phenylimino(triphenyl)phosphorane
Identifiers
CAS Number	2325-27-1
3D model (JSmol)	Interactive image
ChemSpider	67888
ECHA InfoCard	100.017.309
EC Number	219-039-1
PubChem CID	75352
UNII	6L9PT46NGV Y
CompTox Dashboard (EPA)	DTXSID80177820
InChI InChI=1S/C24H20NP/c1-5-13-21(14-6-1)25-26(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20H Key: PTLOPIHJOPWUNN-UHFFFAOYSA-N
SMILES c1ccc(cc1)N=P(c2ccccc2)(c3ccccc3)c4ccccc4
Properties
Chemical formula	C24H20NP
Molar mass	353.405 g·mol−1
Appearance	White solid
Density	1.239 g/cm3
Melting point	131–132 °C (268–270 °F; 404–405 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

The phosphanimines were first prepared in the laboratory of Nobelist Hermann Staudinger. His synthesis involved the direct reaction of triphenylphosphine with phenylazide. ^[1]

Ph₃P + N₃Ph → Ph₃P=NPh + N₂

X-ray crystallography establishes that the P–N–C angle is bent (130.4°) and the P–N distance is 160 pm.^[2]