4141-48-4

Basic information

• Product Name: ALLYLDIPHENYLPHOSPHINE OXIDE
• Synonyms: ALLYLDIPHENYLPHOSPHINE OXIDE;Alydiphenylphosphine oxide;NISTC4141484;Diphenylallylphosphine oxide;[allyl(phenyl)phosphoryl]benzene;[phenyl(prop-2-enyl)phosphoryl]benzene;Diphenyl-2-propenylphosphine oxide;NSC 616249
• CAS NO: 4141-48-4
• Molecular Formula: C₁₅H₁₅OP
• Molecular Weight: 242.25
• Product Categories: Catalysis and Inorganic Chemistry;Phosphine Ligands;Phosphorus Compounds
• Mol File: 4141-48-4.mol
• Article Data: 18

Chemical Properties

• Melting Point: 110-114 °C(lit.)
• Boiling Point: 337 °C at 760 mmHg
• Flash Point: 157.6 °C
• Appearance: /solid
• Density: 1.09 g/cm³
• Vapor Pressure: 0.000211mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: ALLYLDIPHENYLPHOSPHINE OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ALLYLDIPHENYLPHOSPHINE OXIDE(4141-48-4)
• EPA Substance Registry System: ALLYLDIPHENYLPHOSPHINE OXIDE(4141-48-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 4141-48-4(Hazardous Substances Data)

Usage

Description

ALLYLDIPHENYLPHOSPHINE OXIDE is an organic compound that serves as a versatile reagent and intermediate in various chemical reactions and processes. It is characterized by its phosphine oxide group and allyl group, which contribute to its unique chemical properties and reactivity.

Uses

Used in Chemical Synthesis:
ALLYLDIPHENYLPHOSPHINE OXIDE is used as a reactant for the preparation of a-substituted alkylsilanes via regioand chemoselective copper-catalyzed silylzincation and electrophilic substitution from terminal alkenes. This application takes advantage of its reactivity with alkenes and silylzinc reagents to form the desired products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, ALLYLDIPHENYLPHOSPHINE OXIDE is used as a reactant for the preparation of α-substituted alcohols via Fleming-Tamao oxidation of alkylsilanes. This process is crucial for the synthesis of various pharmaceutical compounds, as α-substituted alcohols are important building blocks in drug development.
Used in Catalyst Preparation:
ALLYLDIPHENYLPHOSPHINE OXIDE is used in the olefin isomerization process with Grubbs' catalysts occluded in a hydrophobic matrix of polydimethylsiloxane (PDMS). Its interaction with the catalyst enhances the isomerization efficiency and selectivity, making it a valuable component in this application.
Used in Organic Chemistry:
In organic chemistry, ALLYLDIPHENYLPHOSPHINE OXIDE is used for the synthesis of C9-substituted trans-hydrindene via diastereotopic group-selective intramolecular Diels-Alder reaction. This reaction showcases the compound's ability to participate in complex organic transformations, leading to the formation of valuable synthetic intermediates.
Used in Catalyst Modification:
ALLYLDIPHENYLPHOSPHINE OXIDE is used in the isomerization of allyl group-containing compounds to propenyl group-containing compounds in the presence of a Grubbs second-generation Ru catalyst. This application highlights its role in modifying the catalyst's properties, enabling the selective transformation of allyl groups to propenyl groups.
Used in Material Science:
In material science, ALLYLDIPHENYLPHOSPHINE OXIDE is used in the ruthenium-catalyzed olefin cross-metathesis of vinyl and allyl phosphine oxides to give alkenyl phosphine oxides and bis-phosphine oxides. This process is essential for the development of new materials with specific properties, such as improved stability or reactivity.

InChI:InChI=1/C15H15OP/c1-2-13-17(16,14-9-5-3-6-10-14)15-11-7-4-8-12-15/h2-12H,1,13H2

Upstream product

• 1079-66-9 chloro-diphenylphosphine 
• 1499-21-4 Diphenylphosphinic chloride 
• 762-73-2 trimethyl(allyl)stannane 
• 106-95-6 allyl bromide 
• 4559-70-0 Diphenylphosphine oxide 
• 719-80-2 Ethyl diphenylphosphinite 
• 107-18-6 allyl alcohol 
• 2741-38-0 allyldiphenylphosphine 
• 1498-47-1 allylphosphonic dichloride 
• 14655-53-9 allyloxy-diphenylphosphane 
• 603-35-0 triphenylphosphine 
• 625-38-7 but-3-enoic acid 
• 791-28-6 Triphenylphosphine oxide 
• 15784-26-6 allyl t-butyl carbonate 

Downstream Products

• 54664-14-1 4-(2-diphenylphosphinoyl-1-methyl-ethyl)-morpholine 
• 59971-02-7 Allyl-bis-(m-nitrophenyl)-phosphinoxid 
• 4252-89-5 diphenyl(prop-1-en-1-yl)phosphine oxide 
• 54664-10-7 2-(N-Dimethylamino)propyldiphenylphosphinoxid 
• 54664-11-8 2-(N-Diethylamino)propyldiphenylphosphinoxid 
• 113131-98-9 (E)-1-(diphenylaminophosphinyl)-3-trimethylsilylpropene 
• 1449225-93-7 (E)-3-(dimethylphenylsilyl)-1-(diphenylphosphanoyl)prop-1-ene 
• 1449225-95-9 (E)-2-methyl-6-(diphenylphosphanoyl)hex-5-en-3-ol 
• 1449226-04-3 (E)-1-phenyl-4-(diphenylphosphanoyl)but-3-en-1-ol 
• 1449226-05-4 (E)-4-(diphenylphosphanoyl)-1-(2-thiazolyl)but-3-en-1-ol 
• 1449225-96-0 2-(tributylstannyl)-3-(diphenylphosphanoyl)propan-1-ol 
• 113882-75-0 (E)-(3-hydroxyprop-1-en-1-yl)diphenylphosphine oxide 
• 31614-38-7 1-(diphenylphosphinoyl)propan-2-ol 
• 889-57-6 3-(diphenylphosphinoyl)-1-propanol 

Relevant articles and documents

Use of tin derivatives for selective allylation and methylation of halogenophosphorus compounds

Palladium(0) catalyzed gem-dimethylation of hexachlorocyclotriphosphazene with tetramethylstannane is described as well as the high yield monoallylation of halogenophosphorus or -boron compounds by allyltrialkylstannanes under photolytic conditions.

Synthesis, Structure, and Solution Studies of Lithiated Allylic Phosphines and Phosphine Oxides

This study reports a new series of 12 α-lithiated allylic phosphines and phosphine oxides. By incorporating Lewis base donors including diethyl ether (Et2O), tetrahydrofuran (THF), N,N,N′,N′,-tetramethylethylenediamine (TMEDA), and N,N,N′,N′,N″,-pentamethyldiethylenetriamine (PMDETA), nine complexes were structurally characterized by single-crystal X-ray crystallography. This includes novel dilithiated allylic phosphine 4 [PhP{CHCHCH2Li(TMEDA)}2] and a rare hemisolvated lithiated phosphine oxide 6 [{Ph2P(O)CHC(Me)CH2Li}2(TMEDA)]. Interestingly, in the solid state, P(III) complexes take advantage of Li-πinteractions to the newly formed delocalized system, in comparison to P(V) complexes where the oxophillic nature of the lithium atom dominates. All 12 complexes were fully characterized in the solution state by multinuclear NMR spectroscopy. DFT calculations on isomers of monomeric lithiated complex 3 [Ph2PCHC(Me)CH2Li(PMDETA)] described the low energy barrier between transition steps of the subtle delocalization of the allylic chain.

Ni-Catalyzed C-P Coupling of Aryl, Benzyl, or Allyl Ammonium Salts with P(O)H Compounds

A methodology that allows for the construction of C-P bonds via the nickel-catalyzed cross-coupling of organoammonium salts with appropriate phosphorus nucleophiles has been developed. Aryl-, pyridyl-, benzyl-, and allyl-ammonium triflates can be employed as the electrophiles. The employed phosphorus-based nucleophiles included diaryl/dibutyl phosphine oxide, dialkyl phosphonates, and ethyl phenylphosphinate. Functional groups OMe, CN, CF3, F, Cl, C(O)NMe2, and C(O)tBu were tolerated.

C-P bond-forming reactions via C-O/P-h cross-coupling catalyzed by nickel

The first Ni-catalyzed C-O/P-H cross-coupling producing organophosphorus compounds is disclosed. This method features wide generality in regard to both C-O and P-H compounds: for C-O compounds, the readily available alcohol derivatives of aryl, alkenyl, benzyl, and allyl are applicable, and for P-H compounds, both >PV(O)H compounds (secondary phosphine oxide, H-phosphinate, and H-phosphonate) and hydrogen phosphines (>PIIIH) can be used as the substrates. Thus, a variety of valuable C(sp2)-P and C(sp3)-P compounds can be readily obtained in good to excellent yields by this new strategy.