Ethynyldiphenylphosphine oxide

Base Information

• Chemical Name: Ethynyldiphenylphosphine oxide
• CAS No.: 1351165-67-7
• Molecular Formula: C₂₀H₁₄IOP
• Molecular Weight: 428.209
• Mol file: 1351165-67-7.mol

Synonyms:Ethynyldiphenylphosphine oxide

Chemical Property of Ethynyldiphenylphosphine oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of Ethynyldiphenylphosphine oxide

There total 5 articles about Ethynyldiphenylphosphine 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: 46.0%

1,3-Diiodobenzene (626-00-6) + ethynyl(diphenyl)phosphine oxide (6104-48-9) → Ethynyldiphenylphosphine oxide (1351165-67-7)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisopropylamine; In toluene; at 80 ℃; for 15h; Inert atmosphere;

DOI:10.1021/jo402176w

Reference yield: 38.0%

1,3-Diiodobenzene (626-00-6) + ethynyl(diphenyl)phosphine oxide (6104-48-9) → Ethynyldiphenylphosphine oxide (1351165-67-7) + 1,3-bis[(diphenylphosphoryl)ethynyl]benzene (7608-36-8)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisopropylamine; In toluene; at 80 ℃; for 15h; Inert atmosphere;

DOI:10.1055/s-0030-1261223

Reference yield:

trimethylsilyl(diphenylphosphanyl)acetylene (21037-91-2) → Ethynyldiphenylphosphine oxide (1351165-67-7)

Guidance literature:

Multi-step reaction with 3 steps

1: dihydrogen peroxide / tetrahydrofuran; water / 0 - 20 °C / Air

2: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 0 - 20 °C / Air

3: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisopropylamine / toluene / 15 h / 80 °C / Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; dihydrogen peroxide; diisopropylamine; In tetrahydrofuran; water; toluene; 3: Sonogashira coupling;

DOI:10.1055/s-0030-1261223

upstream raw materials:

1,3-Diiodobenzene

ethynyl(diphenyl)phosphine oxide

trimethylsilyl(diphenylphosphanyl)acetylene

ethynyldiphenylphosphine

Downstream raw materials:

3-(4-methoxyphenylethynyl)phenylethynyldiphenylphosphine oxide

Refernces

• 1、 Peng, Lifen,Xu, Feng,Suzuma, Yoshinori,Orita, Akihiro,Otera, Junzo. "One-pot transformation of Ph2P(O)-protected ethynes: Deprotection followed by transition metal-catalyzed coupling". . p. 12802 - 12808. Retrieved 2014/01/17.