Allyldiphenylphosphine oxide

Base Information

• Chemical Name: Allyldiphenylphosphine oxide
• CAS No.: 4141-48-4
• Molecular Formula: C15H15OP
• Molecular Weight: 242.257
• Hs Code.: 2902909090
• European Community (EC) Number: 627-599-7
• NSC Number: 98715,616249
• DSSTox Substance ID: DTXSID60194338
• Nikkaji Number: J80.762A
• Wikidata: Q83067105
• Mol file: 4141-48-4.mol

Synonyms:Allyldiphenylphosphine oxide;4141-48-4;[phenyl(prop-2-enyl)phosphoryl]benzene;NSC616249;Diphenyl-2-propenylphosphine oxide;NSC 98715;allyldiphenyl phosphine oxide;NCIOpen2_006458;Allyl Diphenylphosphine Oxide;Allyl(diphenyl)phosphine oxide;SCHEMBL1652829;[allyl(phenyl)phosphoryl]benzene;DTXSID60194338;PGPAPANRSWMTQO-UHFFFAOYSA-N;Allyldiphenylphosphine oxide, 97%;NSC98715;MFCD00013908;NSC-98715;AKOS024264204;NSC-616249;CS-0086083;FT-0635149;T70896

Chemical Property of Allyldiphenylphosphine oxide

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 0.000211mmHg at 25°C
• Melting Point: 110-114 °C(lit.)
• Refractive Index: 1.564
• Boiling Point: 337 °C at 760 mmHg
• Flash Point: 157.6 °C
• PSA: 26.88000
• Density: 1.09 g/cm³
• LogP: 3.18650
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 242.086052095
• Heavy Atom Count: 17
• Complexity: 263

Purity/Quality:

98%,99%, ^*data from raw suppliers

Allyldiphenylphosphine Oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CCP(=O)(C1=CC=CC=C1)C2=CC=CC=C2
• 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 alkylsilanesOlefin isomerization with Grubbs′ catalysts occluded in a hydrophobic matrix of polydimethylsiloxane (PDMS)C9-substituted trans-hydrindene via diastereotopic group-selective intramolecular Diels-Alder reactionIsomerization of allyl group-containing compounds to propenyl group-containing compounds in the presence of a Grubbs second-generation Ru catalystRuthenium-catalyzed olefin cross-metathesis of vinyl and allyl phosphine oxides to give alkenyl phosphine oxides and bis-phosphine oxides

Technology Process of Allyldiphenylphosphine oxide

There total 21 articles about Allyldiphenylphosphine oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

trimethyl(allyl)stannane (762-73-2) + Diphenylphosphinic chloride (1499-21-4) → allyldiphenylphosphine oxide (4141-48-4)

Guidance literature:

In toluene; Irradiation; other chlorophosphorus derivatives;

DOI:10.1016/S0040-4039(00)74728-9

Reference yield: 94.0%

N,N,N-trimethylprop-2-en-1-ammonium triflate + Diphenylphosphine oxide (4559-70-0) → allyldiphenylphosphine oxide (4141-48-4)

Guidance literature:

With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; caesium carbonate; In acetonitrile; at 80 ℃; for 18h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.joc.8b02926

Reference yield: 91.0%

allyl bromide (106-95-6) + Triphenylphosphine oxide (791-28-6) → allyldiphenylphosphine oxide (4141-48-4)

Guidance literature:

Triphenylphosphine oxide; With sodium hydride; lithium iodide; In tetrahydrofuran; at 60 ℃; for 13h; Inert atmosphere;

allyl bromide; In tetrahydrofuran; at 0 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1039/c8cc00289d

upstream raw materials:

allyloxy-diphenylphosphane

allylphosphonic dichloride

allyldiphenylphosphine

chloro-diphenylphosphine

Downstream raw materials:

5-diphenylphosphinoylmethyl-3-propyl-4,5-dihydroisoxazole

(2,3-Dihydroxy-propyl)-diphenylphosphinoxid

β-Piperidinoethyldiphenylphosphine oxide

3-diphenylphosphinoyl-2-methyl-4-piperidinobutan-2-ol

Refernces

• 1、 Giguere,Herberich. "Microwave heating in synthesis: Preparation of allyldiphenylphosphine oxide". . p. 2197 - 2201. Retrieved 1991.
• 2、 Yang, Bo,Wang, Zhong-Xia. "Ni-Catalyzed C-P Coupling of Aryl, Benzyl, or Allyl Ammonium Salts with P(O)H Compounds". . p. 1500 - 1509. Retrieved 2019/02/07.
• 3、 Tejo, Ciputra,Pang, Jia Hao,Ong, Derek Yiren,Oi, Miku,Uchiyama, Masanobu,Takita, Ryo,Chiba, Shunsuke. "Dearylation of arylphosphine oxides using a sodium hydride-iodide composite". supporting information. p. 1782 - 1785. Retrieved 2018/02/21.