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| | Allyldiphenylphosphine oxide Basic information |
| | Allyldiphenylphosphine oxide Chemical Properties |
| Melting point | 110-114 °C(lit.) | | Boiling point | 200-202 °C(Press: 2 Torr) | | density | 1.0769 g/cm3 | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | solubility | sol THF; slightly sol ether; insol hexane. | | form | solid | | Appearance | White to off-white Solid | | InChI | InChI=1S/C15H15OP/c1-2-13-17(16,14-9-5-3-6-10-14)15-11-7-4-8-12-15/h2-12H,1,13H2 | | InChIKey | PGPAPANRSWMTQO-UHFFFAOYSA-N | | SMILES | P(=O)(C1=CC=CC=C1)(C1=CC=CC=C1)CC=C |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | Storage Class | 13 - Non Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | Allyldiphenylphosphine oxide Usage And Synthesis |
| Uses | Reactant for:
- Preparaton of a-substituted alkylsilanes via regio- and chemoselective copper-catalyzed silylzincation and electrophilic substitution from terminal alkenes, and prepn. of α-substituted alcohols via Fleming-Tamao oxidation of alkylsilanes
- Olefin isomerization with Grubbs′ catalysts occluded in a hydrophobic matrix of polydimethylsiloxane (PDMS)
- C9-substituted trans-hydrindene via diastereotopic group-selective intramolecular Diels-Alder reaction
- Isomerization of allyl group-containing compounds to propenyl group-containing compounds in the presence of a Grubbs second-generation Ru catalyst
- Ruthenium-catalyzed olefin cross-metathesis of vinyl and allyl phosphine oxides to give alkenyl phosphine oxides and bis-phosphine oxides
| | reaction suitability | reagent type: ligand | | Synthesis | The synthesis method of Allyldiphenylphosphine Oxide: (1) rearrangement of allyl diphenylphosphinite and (2) Arbuzov reaction of alkyl diphenylphosphinite with Allyl Bromide. Other new methods have also been developed. Structurally related analogs prepared include 2- methylallyldiphenylphosphine oxide, 2-phenylallyldiphenylphosphine oxide, 1- methoxyallyldiphenylphosphine oxide, crotyldiphenylphosphine oxide, and 1-substituted allylic diphenylphosphine oxide[1]. | | Synthesis | Purification: recrystallization from ether/hexane, benzene/petroleum ether, cyclohexane, or benzene[2].
| | References |
1. (a) Ukai, J.; Ikeda, Y.; Ikeda, N.; Yamamoto, H. TL 1983, 24, 4029. (b) Ikeda, Y.; Ukai, J.; Ikeda, N.; Yamamoto, H. T 1987, 43, 723. (c) Burke, S. D.; Armistead, D. M.; Shankaran, K. TL 1986, 27, 6295.
2. Berlin, K. D.; Calvert, J. F. Proc. Okla. Acad. Sci. 1966, 46, 78
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| | Allyldiphenylphosphine oxide Preparation Products And Raw materials |
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