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Diphenylphosphine oxide

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Diphenylphosphine oxide
Ball-and-stick model of the diphenylphosphine oxide molecule
Names
Preferred IUPAC name Diphenyl-λ-phosphanone
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
InChI
  • InChI=1S/C12H11OP/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,14HKey: ASUOLLHGALPRFK-UHFFFAOYSA-N
SMILES
  • c1ccc(cc1)P(=O)c2ccccc2
Properties
Chemical formula 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 , 100 kPa). Infobox references
Chemical compound

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

Synthesis

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

(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 or diphenylphosphine.

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.

Thionyl chloride converts diphenylphosphine oxide to chlorodiphenylphosphine.

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

References

  1. ^ Saunders, Jeffrey O.; Wang, Zheng; Ding, Kuiling (2007). "Diphenylphosphine Oxide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd428.pub2. ISBN 978-0-471-93623-7.
  2. Hunt, B. B.; Saunders, B. C. (1957). "Preparation and Reactions of Diphenylphosphine Oxide". J. Chem. Soc.: 2413–2414. doi:10.1039/JR9570002413.
  3. 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.
  4. Carl A. Busacca; Jon C. Lorenz; Paul Sabila; Nizar Haddad; Chris H. Senanyake (2007). "Synthesis Of Electron-Deficient Secondary Phosphine Oxides And Secondary Phosphines: Bisphosphine Oxide And Bisphosphine". Org. Synth. 84: 242. doi:10.15227/orgsyn.084.0242.
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