Phenylphosphine
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Names | |||
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Preferred IUPAC name
Phenylphosphane | |||
Other names
Phenylphosphine
Monophenylphosphine | |||
Identifiers | |||
3D model (JSmol)
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ChemSpider | |||
ECHA InfoCard | 100.010.297 | ||
EC Number |
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PubChem CID
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RTECS number |
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UNII | |||
UN number | 2924 | ||
CompTox Dashboard (EPA)
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Properties | |||
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) | ||
Hazards | |||
GHS labelling: | |||
Signal word
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Warning | ||
H250, H301, H311, H315, H319, H331, H335 | |||
P210, P222, P261, P264, P270, P271, P280, P301+P310, P302+P334, P302+P352, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P370+P378, P403+P233, P405, P422, P501 | |||
NIOSH (US health exposure limits): | |||
PEL (Permissible)
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none[1] | ||
REL (Recommended)
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C 0.05 ppm (0.25 mg/m3)[1] | ||
IDLH (Immediate danger)
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N.D.[1] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
what is ?) | (|||
Infobox references | |||
Phenylphosphine is an organophosphorus compound with the chemical formula C6H5PH2. It is the phosphorus analog of aniline. Like other , 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.[2]
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.[3]
Reactions[]
Oxidation of phenylphosphine with air affords the oxide.[3]
- 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.[4]
Phenylphosphine reacts with many metal complexes to give complexes and clusters.[5] 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.[6]
References[]
- ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0501". National Institute for Occupational Safety and Health (NIOSH).
- ^ Svara, Jürgen; Weferling, Norbert ; Hofmann, Thomas "Phosphorus Compounds, Organic" in Ullmann's Encyclopedia of Industrial Chemistry. John Wiley & Sons, Inc., 2008. doi:10.1002/14356007
- ^ a b Freedman, Leon D.; Doak, G. O. (1952). "The Reduction of Benzenephosphonyl Dichloride". Journal of the American Chemical Society. 74 (13): 3414–3415. doi:10.1021/ja01133a504.
- ^ Snider, Theodore E.; Morris, Don L.; Srivastava, K. C. & Berlin, K. D. (1988). "1-Phenyl-4-Phosphorinanone". Organic Syntheses.; Collective Volume, 6, p. 932
- ^ Schumann, Herbert; Schwabe, Peter; Stelzer, Othmar (1969). "Organogermyl, stannyl und plumbylphosphine". Chemische Berichte. 102 (9): 2900–2913. doi:10.1002/cber.19691020904.
- ^ Obata, Takatsugu; Kobayashi, Eiichi; Aoshima, Sadahito; Furukawa, Junji (1994). "Synthesis of new linear polymers containing phosphorus atom in the main chain by the radical polyaddition: Addition polymers of phenylphosphine with 1,4-divinylbenzene or 1,4-diisopropenylbenzene and their properties". Journal of Polymer Science Part A: Polymer Chemistry. 32 (3): 475–483. doi:10.1002/pola.1994.080320309.
- Phosphines
- Foul-smelling chemicals