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. 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.

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