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.
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.[2]
Reactionsedit
Oxidation of phenylphosphine with air affords the oxide.[2]
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.[3]
Phenylphosphine reacts with many metal complexes to give complexes and clusters.[4] It is the precursor to the bridging phosphinidene ligand in certain clusters.
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.[5]
^ abFreedman, 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; Collected Volumes, vol. 6, p. 932.
^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. Bibcode:1994JPoSA..32..475O. doi:10.1002/pola.1994.080320309.
April 14, 2024
phenylphosphine, organophosphorus, compound, with, chemical, formula, c6h5ph2, phosphorus, analog, aniline, like, other, primary, phosphines, phenylphosphine, intense, penetrating, odor, highly, oxidizable, mainly, used, precursor, other, organophosphorus, com. 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 Phenylphosphine NamesPreferred IUPAC name PhenylphosphaneOther names PhenylphosphineMonophenylphosphineIdentifiersCAS Number 638 21 1 Y3D model JSmol Interactive imageChemSpider 12002 YECHA InfoCard 100 010 297EC Number 211 325 4PubChem CID 12519RTECS number SZ2100000UNII 856X9KP929 YUN number 2924CompTox Dashboard EPA DTXSID7073224InChI InChI 1S C6H7P c7 6 4 2 1 3 5 6 h1 5H 7H2 NKey RPGWZZNNEUHDAQ UHFFFAOYSA N NInChI 1 C6H7P c7 6 4 2 1 3 5 6 h1 5H 7H2Key RPGWZZNNEUHDAQ UHFFFAOYAHSMILES C1 CC C C C1 PPropertiesChemical formula C6H5PH2Molar mass 110 09 g molAppearance Colorless liquidOdor foulDensity 1 001 g cm3Boiling point 160 C 320 F 433 K HazardsGHS labelling PictogramsSignal word WarningHazard statements H250 H301 H311 H315 H319 H331 H335Precautionary statements 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 P501NIOSH US health exposure limits PEL Permissible none 1 REL Recommended C 0 05 ppm 0 25 mg m3 1 IDLH Immediate danger N D 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesSynthesis editPhenylphosphine 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 2 Reactions editOxidation of phenylphosphine with air affords the oxide 2 C6H5PH2 O2 C6H5P OH 2Bis 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 2Bis 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 3 Phenylphosphine reacts with many metal complexes to give complexes and clusters 4 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 HClPhenylphosphine 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 5 References edit a b c NIOSH Pocket Guide to Chemical Hazards 0501 National Institute for Occupational Safety and Health NIOSH 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 amp Berlin K D 1988 1 Phenyl 4 Phosphorinanone Organic Syntheses Collected Volumes vol 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 Bibcode 1994JPoSA 32 475O doi 10 1002 pola 1994 080320309 Retrieved from https en wikipedia org w index php title Phenylphosphine amp oldid 1209329756, wikipedia, wiki, book, books, library,
