Diphenylphosphine oxide

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Diphenylphosphine oxide
Diphenylphosphine-oxide-2D-skeletal.svg
Ball-and-stick model of the diphenylphosphine oxide molecule Diphenylphosphine-oxide-from-xtal-Mercury-3D-bs.png
Ball-and-stick model of the diphenylphosphine oxide molecule
Names
Preferred IUPAC name
Diphenyl-λ5-phosphanone
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
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
Appearancewhite 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).

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]

Contents

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

  1. 1 2 3 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: 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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