Phenylphosphine

Phenylphosphine

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Names
Other names Monophenylphosphine
Identifiers
CAS Number	638-21-1 Y
ChemSpider	12002 N
EC Number	211-325-4
Jmol 3D model	Interactive image
PubChem	12519
InChI InChI=1S/C6H7P/c7-6-4-2-1-3-5-6/h1-5H,7H2 N Key: RPGWZZNNEUHDAQ-UHFFFAOYSA-N N InChI=1/C6H7P/c7-6-4-2-1-3-5-6/h1-5H,7H2 Key: RPGWZZNNEUHDAQ-UHFFFAOYAH
SMILES C1=CC=C(C=C1)P
Properties
Chemical formula	C6H5PH2
Molar mass	110.09 g/mol
Appearance	Colorless liquid
Odor	foul
Density	1.001 g/cm3
Boiling point	160 °C (320 °F; 433 K)
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Phenylphosphine is an organophosphorus compound with the chemical formula C₆H₅PH₂. It is the phosphorus analog of aniline. Like other primary phosphines, phenylphosphine has an intense penetrating odor and is highly oxidizable. It is mainly used as a precursor to other organophosphorus compounds. It can function as a ligand in coordination chemistry.

Synthesis

Phenylphosphine can be produced by reducing dichlorophenylphosphine with lithium aluminum hydride in ether:

LiAlH₄ + 2C₆H₅PCl₂ → 2C₆H₅PH₂ + Li⁺ + Al³⁺ + 4Cl⁻

This reaction is performed under a nitrogen atmosphere to prevent side reactions involving oxygen.

Reactions

Oxidation of phenylphosphine with air affords the oxide.

C₆H₅PH₂ + O₂ → C₆H₅P(OH)₂

Bis(2-cyanoethylphenyl)phosphine, which is of interest as a synthetic intermediate, can be made from phenylphosphine by base-catalyzed allylic addition to acrylonitrile.

C₆H₅PH₂ + 2CH₂=CHCN → C₆H₅P(CH₂CH₂CN)₂

Bis(2-cyanoethylphenyl)phosphine is a useful precursor to 1-phenyl-4-phosphorinanone by base-induced cyclization followed by hydrolysis. Phosphorinanones can be used to prepare alkenes, amines, indoles, and secondary and tertiary alcohols by reduction, Grignard, and Reformatsky reagents.

Phenylphosphine reacts with many metal complexes to give complexes and clusters. It is the precursor to the bridging phosphinidene ligand in certain clusters.

2 (C₆H₅)₂MCl + C₆H₅PH₂ + 3 (C₂H₅)₃N → ((C₆H₅)₂M)₂PC₆H₅ + 3 (C₂H₅)₃N•HCl

Phenylphosphine also have uses in polymer synthesis. Using radical initiations or UV irradiation, polyaddition of phenylphosphine to 1,4-divinylbenzene or 1,4-diisopropenylbenzene will form phosphorus-containing polymers, which have self-extinguishing properties. When mixed with flammable polymers such as polystyrene and polyethylene, the mixed polymer exhibits flame resistant properties.