Diphenylphosphine oxide
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Properties | |
C12H11OP | |
Molar mass | 202.19 |
Appearance | white solid |
Melting point | 56-57 ºC |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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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.
Organophosphinous acids are deoxygenated with DIBAH. The resulting secondary phosphines are precursors to phosphine ligands.[2]
References
- ↑ 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
- ↑ Carl A. Busacca, Jon C. Lorenz, Paul Sabila, Nizar Haddad, Chris H. Senanyake (2007). "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". Org. Synth. 84: 242. doi:10.15227/orgsyn.084.0242.
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