| Identification | Back Directory | [Name]
ALLYLDIPHENYLPHOSPHINE OXIDE | [CAS]
4141-48-4 | [Synonyms]
NSC 98715
NSC 616249
NISTC4141484
Alydiphenylphosphine oxide
ALLYLDIPHENYLPHOSPHINE OXIDE
Diphenylallylphosphine oxide
[allyl(phenyl)phosphoryl]benzene
Allyldiphenylphosphine oxide 97%
Allyldiphenylphosphine Oxide >
Diphenyl-2-propenylphosphine oxide
[phenyl(prop-2-enyl)phosphoryl]benzene
Phosphine oxide,diphenyl-2-propen-1-yl- | [Molecular Formula]
C15H15OP | [MDL Number]
MFCD00013908 | [MOL File]
4141-48-4.mol | [Molecular Weight]
242.25 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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]
Purification: recrystallization from ether/hexane, benzene/petroleum ether, cyclohexane, or benzene[2].
| [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]. | [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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