| 词条 | Diphenylphosphine oxide |
| 释义 |
| ImageFile = Diphenylphosphine oxide.png | ImageSize = | ImageAlt = | IUPACName = | OtherNames = |Section1={{Chembox Identifiers | CASNo = 4559-70-0 | PubChem = 254003 | ChemSpiderID = 222625 | SMILES = c1ccc(cc1)P(=O)c2ccccc2 | StdInChI = 1S/C12H11OP/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,14H | StdInChIKey = ASUOLLHGALPRFK-UHFFFAOYSA-N }} |Section2={{Chembox Properties |C = 12|H = 11|O = 1|P = 1 | MolarMass = 202.19 | Appearance = white solid | Density = | MeltingPt = 56-57 ºC | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} Diphenylphosphine oxide is an organophosphorus compound with the formula (C6H5)2P(O)H. It is a white solid that soluble in polar organic solvents. The compound is used in Buchwald-Hartwig coupling reactions to introduce a diphenylphosphino substituent.[1] Analogous to the behavior of phosphorous acid, diphenylphosphine oxide exists in equilibrium with a minor tautomer hydroxydiphenylphosphine (CAS#24630-80-6) (C6H5)2POH. SynthesisDiphenylphosphine oxide can be prepared by the reaction of phosphonic esters, such as diethylphosphite, with Grignard reagents. Alternatively, it may be prepared by the partial hydrolysis of chlorodiphenylphosphine[1] or diphenylphosphine.[2] ReactionsOrganophosphinous acids are deoxygenated with DIBAH. The resulting secondary phosphines are precursors to phosphine ligands.[3] References1. ^1 Jeffrey O. Saunders, Zheng Wang, Kuiling Ding "Diphenylphosphine Oxide" Encyclopedia of Reagents for Organic Synthesis, 2007 John Wiley & Sons, Ltd.{{DOI|10.1002/047084289X.rd428.pub2}} 2. ^{{cite journal |last1=RAUHUT |first1=M. M. |last2=CURRIER |first2=HELEN A. |title=Oxidation of Secondary Phosphines to Secondary Phosphine Oxides |journal=The Journal of Organic Chemistry |date=November 1961 |volume=26 |issue=11 |pages=4626–4628 |doi=10.1021/jo01069a102}} 3. ^{{cite journal|title=Synthesis Of Electron-Deficient Secondary Phosphine Oxides And Secondary Phosphines: Bis[3,5-bis(Trifluoromethyl)phenyl]phosphine Oxide And Bis[3,5-bis(Trifluoromethyl)phenyl]phosphine|authors=Carl A. Busacca, Jon C. Lorenz, Paul Sabila, Nizar Haddad, Chris H. Senanyake|journal=Org. Synth.|year=2007|volume=84|page=242|doi=10.15227/orgsyn.084.0242}} 2 : Organophosphine oxides|Phenyl compounds |
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