ALLYLDIPHENYLPHOSPHINE OXIDE Property

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

ALLYLDIPHENYLPHOSPHINE OXIDE Chemical Properties,Usage,Production

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

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