Divinylphenylphosphine

Base Information

• Chemical Name: Divinylphenylphosphine
• CAS No.: 26681-88-9
• Molecular Formula: C10H11P
• Molecular Weight: 162.171
• Hs Code.: 2902909090
• European Community (EC) Number: 247-900-1
• UNII: CX6D8PAZ53
• DSSTox Substance ID: DTXSID90949499
• Nikkaji Number: J248.996A
• Wikidata: Q72470257
• Mol file: 26681-88-9.mol

Synonyms:Divinylphenylphosphine;26681-88-9;Phenyldivinylphosphine;bis(ethenyl)-phenylphosphane;CX6D8PAZ53;EINECS 247-900-1;diethenyl(phenyl)phosphane;UNII-CX6D8PAZ53;Phosphine, diethenylphenyl-;DIETHENYLPHENYLPHOSPHINE;SCHEMBL957926;PHOSPHINE, PHENYLDIVINYL-;C10H11P;DTXSID90949499;C10-H11-P;AKOS015915700;FT-0638628;J-016511

Chemical Property of Divinylphenylphosphine

Chemical Property:

• Vapor Pressure: 0.308mmHg at 25°C
• Refractive Index: n20/D 1.582(lit.)
• Boiling Point: 208.4 °C at 760 mmHg
• Flash Point: 80.9 °C
• PSA: 13.59000
• Density: 0.979 g/mL at 25 °C(lit.)
• LogP: 3.08080
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 162.059837349
• Heavy Atom Count: 11
• Complexity: 126

Purity/Quality:

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

Divinylphenylphosphine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CP(C=C)C1=CC=CC=C1
• Uses: Reactant for:Synthesis of P-chiral phosphines via chiral metal template promoted asymmetric furan Diels-Alder reaction

Technology Process of Divinylphenylphosphine

There total 3 articles about Divinylphenylphosphine 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: 20.0%

(OC)5WPPh(CH=CH2)2 (79919-73-6) + W(CO)5(PPh2H) (18399-62-7) + diphenylphosphane (829-85-6) → (OC)5WPPh2CH2CH2PPhCH2CH2PPh2 (79919-65-6) + divinylphenylphosphine (26681-88-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In neat (no solvent); under N2 atm. mixt. (OC)5WPPh(CH=CH2)2, PPh2H and 2,2'-azobis(isobutyronitrile) heated for 24 h at 75°C, excess PhP(CH=CH2)2 removed under high vac. after which (OC)5WPPh2H and AIBN added and mixt. heated for24 h at 75°C; oil dissolved in min. CH2Cl2 and CH3OH and refrigerated at 6°C;

DOI:10.1021/ic00133a075

Reference yield:

vinyl magnesium bromide (1826-67-1) + Dichlorophenylphosphine (644-97-3) → divinylphenylphosphine (26681-88-9)

Guidance literature:

DOI:10.1021/ja01579a012

Reference yield:

diethyl phenylphosphonite (1638-86-4) + vinyl magnesium bromide (1826-67-1) → divinylphenylphosphine (26681-88-9)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃; Reflux; Inert atmosphere;

DOI:10.1021/ic2027169

upstream raw materials:

vinyl magnesium bromide

Dichlorophenylphosphine

(OC)5WPPh(CH=CH₂)2

W(CO)5(PPh2H)

Downstream raw materials:

bis<(diethylphosphino)ethyl>phenylphosphine

bis(2-((2S,5S)-2,5-dimethylphospholanoethyl))phenylphosphine

bis<(dicyclohexylphosphino)ethyl>phenylphosphine

[(η6-C6H6)RuCl2(DVPP)]

Refernces

• 1、 Keiter, Richard L.,Brodack, James W.,Borger, Rodney D.,Gary, Lew W.. "Controlling the number of metal sites to which Ph2PCH2CH2PPhCH2CH 2PPh2 coordinates in tungsten carbonyls". . p. 1256 - 1259. Retrieved 2008/10/08.