2,5-bis(hex-1'-ynyl)-1,4-diacetoxybenzene

Base Information

• Chemical Name: 2,5-bis(hex-1'-ynyl)-1,4-diacetoxybenzene
• CAS No.: 925900-92-1
• Molecular Formula: C₂₂H₂₆O₄
• Molecular Weight: 354.446
• Mol file: 925900-92-1.mol

Synonyms:2,5-bis(hex-1'-ynyl)-1,4-diacetoxybenzene

Chemical Property of 2,5-bis(hex-1'-ynyl)-1,4-diacetoxybenzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,5-bis(hex-1'-ynyl)-1,4-diacetoxybenzene

There total 2 articles about 2,5-bis(hex-1'-ynyl)-1,4-diacetoxybenzene 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: 84.0%

2,5-dibromohydroquinone diacetate (40101-03-9) + hex-1-yne (693-02-7) → 2,5-bis(hex-1'-ynyl)-1,4-diacetoxybenzene (925900-92-1)

Guidance literature:

With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 80 ℃; for 24h;

DOI:10.1016/j.tet.2006.11.016

Reference yield:

2,5-dibromohydroquinone (14753-51-6) → 2,5-bis(hex-1'-ynyl)-1,4-diacetoxybenzene (925900-92-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / Et₃N / CH₂Cl₂; diethyl ether / 1.5 h / 20 °C

2: 84 percent / Et₃N; CuI / PdCl₂(PPh₃)2 / dimethylformamide / 24 h / 80 °C

With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; 2: Sonogashira coupling;

DOI:10.1016/j.tet.2006.11.016

Reference yield: 80.0%

2,5-bis(hex-1'-ynyl)-1,4-diacetoxybenzene (925900-92-1) → 2,5-bis(hex-1'-ynyl)-1,4-dihydroxybenzene (925900-81-8)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; water; at 0 ℃; for 0.333333h;

DOI:10.1016/j.tet.2006.11.016

upstream raw materials:

2,5-dibromohydroquinone diacetate

hex-1-yne

2,5-dibromohydroquinone

Downstream raw materials:

2,5-bis(hex-1'-ynyl)-1,4-dihydroxybenzene

1,4-bis(allyloxy)-2,5-di(hex-1'-ynyl)benzene

2,5-bis(hex-1'-ynyl)-1,4-bis(pent-4'-enyloxy)benzene

Refernces

• 1、 Liang, Zhiqiang,Ma, Shengming,Yu, Jihong,Xu, Ruren. "Double annulations of dihydroxy- and diacetoxy-dialkynylbenzenes. An efficient construction of benzodifurans". . p. 12877 - 12882. Retrieved 2008/03/28.