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Diphenylphosphine oxide

Chemical compound From Wikipedia, the free encyclopedia

Diphenylphosphine oxide is an organophosphorus compound with the formula (C6H5)2P(O)H. It is a white solid that is soluble in polar organic solvents.[1]

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Diphenylphosphine oxide
Ball-and-stick model of the diphenylphosphine oxide molecule
Ball-and-stick model of the diphenylphosphine oxide molecule
Names
Preferred IUPAC name
Diphenyl-λ5-phosphanone
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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
  • c1ccc(cc1)P(=O)c2ccccc2
Properties
C12H11OP
Molar mass 202.19
Appearance white solid
Melting point 56-57 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis

Diphenylphosphine oxide can be prepared by the reaction of phosphonic esters, such as diethylphosphite, with Grignard reagents followed by acid workup:[2]

(C2H5O)2P(O)H + 3 C6H5MgBr → (C6H5)2P(O)MgBr + C2H5OMgBr
(C6H5)2P(O)MgBr + HCl → (C6H5)2P(O)H + MgBrCl

Alternatively, it may be prepared by the partial hydrolysis of chlorodiphenylphosphine[1] or diphenylphosphine.[3]

Reactions

Diphenylphosphine oxide exists in equilibrium with its minor tautomer diphenylphosphinous acid, ((C6H5)2POH:

(C6H5)2P(O)H ⇌ (C6H5)2POH

Diphenylphosphine oxide is used in Buchwald-Hartwig coupling reactions to introduce diphenylphosphino substituents.[1]

Thionyl chloride converts diphenylphosphine oxide to chlorodiphenylphosphine.

Organophosphinous acids are deoxygenated with DIBAH. The resulting secondary phosphines are precursors to phosphine ligands.[4]

References

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