Diphenylphosphine oxide

Diphenylphosphine oxide
Identifiers
CAS Number	4559-70-0;
3D model (JSmol)	Interactive image;
ChemSpider	222625;
PubChem CID	254003;
	InChI InChI=1S/C12H11OP/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,14H Key: ASUOLLHGALPRFK-UHFFFAOYSA-N;
	SMILES c1ccc(cc1)P(=O)c2ccccc2;
Properties
Chemical formula	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).
	Infobox references

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.

Synthesis

Diphenylphosphine 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]

Reactions

Organophosphinous acids are deoxygenated with DIBAH. The resulting secondary phosphines are precursors to phosphine ligands.[3]

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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
RAUHUT, M. M.; CURRIER, HELEN A. (November 1961). "Oxidation of Secondary Phosphines to Secondary Phosphine Oxides". The Journal of Organic Chemistry. 26 (11): 4626–4628. doi:10.1021/jo01069a102.
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.CS1 maint: uses authors parameter (link)

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[e-EROS-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] RAUHUT, M. M.; CURRIER, HELEN A. (November 1961). "Oxidation of Secondary Phosphines to Secondary Phosphine Oxides". The Journal of Organic Chemistry. 26 (11): 4626–4628. doi:10.1021/jo01069a102.

[3] 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.CS1 maint: uses authors parameter (link)