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ChemicalBook--->CAS DataBase List--->4141-48-4

4141-48-4

4141-48-4 Structure

4141-48-4 Structure
IdentificationBack 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 PropertiesBack 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
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319
[Precautionary statements ]

P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26-36
[WGK Germany ]

3
Hazard InformationBack 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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