Phenylphosphine
Encyclopedia
Phenylphosphine is a primary phosphine
with the chemical formula C6H5PH2. It is the phosphorus analog of aniline
. Like all other primary phosphines, phenylphosphine has an intense penetrating odor. Its chemistry is very similar to other primary phosphines: it is highly oxidizable, it can function as ligands in complexes, and it is highly nucleophilic.
with lithium aluminum hydride at the reflux temperature of ether.
This reaction must be performed under a nitrogen atmosphere as phenylphosphine can be oxidized by oxygen.
Bis(2-cyanoethylphenyl)phosphine is useful in synthesis as it can be used to prepare 1-phenyl-4-phosphorinanone. This is done by first refluxing the bis(2-cyanoethylphenyl)phosphine in toluene with potassium tert-butoxide
followed by vigorous reflux with 6 N HCl. Phosphorinanones are very useful synthetic intermediates as they can be used to prepare alkenes, amines, indoles, and secondary and tertiary alcohols by reduction, Grignard
, and Reformatsky reagents.
Phenylphophine can also be used to prepare benzenephosphonous acid by oxidation with air.
Phenylphosphine can function as ligands in Ge, Sn, and Pb complexes. The phenylphosphine complexes of Ge, Sn, and Pb will from metal clusters. The phenylphosphine ligand will bridge two metal atoms.
+ 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. Phosphorus-containing polymers have self-extinguishing properties. When mixed with flammable polymers such as polystyrene and polyethylene, the mixed polymer exhibit flame resistant properties.
Phosphine
Phosphine is the compound with the chemical formula PH3. It is a colorless, flammable, toxic gas. Pure phosphine is odourless, but technical grade samples have a highly unpleasant odor like garlic or rotting fish, due to the presence of substituted phosphine and diphosphine...
with the chemical formula C6H5PH2. It is the phosphorus analog of aniline
Aniline
Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of precursors to polyurethane...
. Like all other primary phosphines, phenylphosphine has an intense penetrating odor. Its chemistry is very similar to other primary phosphines: it is highly oxidizable, it can function as ligands in complexes, and it is highly nucleophilic.
Synthesis
Phenylphosphine can be produced by reducing dichlorophenylphosphineDichlorophenylphosphine
Dichlorophenylphosphine is an organophosphorus compound with the formula C6H5PCl2. This colourless viscous liquid is commonly used in the synthesis of phosphine ligands....
with lithium aluminum hydride at the reflux temperature of ether.
- LiAlH4 + 2C6H5PCl2 → 2C6H5PH2 + Li+ + Al3+ + 4Cl-
This reaction must be performed under a nitrogen atmosphere as phenylphosphine can be oxidized by oxygen.
Reactions
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 useful in synthesis as it can be used to prepare 1-phenyl-4-phosphorinanone. This is done by first refluxing the bis(2-cyanoethylphenyl)phosphine in toluene with potassium tert-butoxide
Potassium tert-butoxide
Potassium tert-butoxide is the chemical compound with the formula 3COK. This colourless solid is a strong base useful in organic synthesis. It exists as a tetrameric cubane-like cluster...
followed by vigorous reflux with 6 N HCl. Phosphorinanones are very useful synthetic intermediates as they can be used to prepare alkenes, amines, indoles, and secondary and tertiary alcohols by reduction, Grignard
Grignard reaction
The Grignard reaction is an organometallic chemical reaction in which alkyl- or aryl-magnesium halides add to a carbonyl group in an aldehyde or ketone. This reaction is an important tool for the formation of carbon–carbon bonds...
, and Reformatsky reagents.
Phenylphophine can also be used to prepare benzenephosphonous acid by oxidation with air.
- C6H5PH2 + O2 → C6H5P(OH)2
Phenylphosphine can function as ligands in Ge, Sn, and Pb complexes. The phenylphosphine complexes of Ge, Sn, and Pb will from metal clusters. The phenylphosphine ligand will bridge two metal atoms.
- 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. Phosphorus-containing polymers have self-extinguishing properties. When mixed with flammable polymers such as polystyrene and polyethylene, the mixed polymer exhibit flame resistant properties.