1,1'-hexyl-6,6'-[(1,4-bis(dodecyloxy)-2,5-phenylene)diethynyl]bisuracil

Base Information

• Chemical Name: 1,1'-hexyl-6,6'-[(1,4-bis(dodecyloxy)-2,5-phenylene)diethynyl]bisuracil
• CAS No.: 1290140-53-2
• Molecular Formula: C₅₄H₈₂N₄O₆
• Molecular Weight: 883.268
• Mol file: 1290140-53-2.mol

Synonyms:1,1'-hexyl-6,6'-[(1,4-bis(dodecyloxy)-2,5-phenylene)diethynyl]bisuracil

Chemical Property of 1,1'-hexyl-6,6'-[(1,4-bis(dodecyloxy)-2,5-phenylene)diethynyl]bisuracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,1'-hexyl-6,6'-[(1,4-bis(dodecyloxy)-2,5-phenylene)diethynyl]bisuracil

There total 11 articles about 1,1'-hexyl-6,6'-[(1,4-bis(dodecyloxy)-2,5-phenylene)diethynyl]bisuracil 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: 77.0%

1-hexyl-6-iodo-2,4(1H,3H)-pyrimidinedione (1091632-52-8) + 1,4-bis(dodecyloxy)-2,5-diethynylbenzene (152270-00-3) → 1,1'-hexyl-6,6'-[(1,4-bis(dodecyloxy)-2,5-phenylene)diethynyl]bisuracil (1290140-53-2)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In tetrahydrofuran; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ja2011516

Reference yield: 40.3%

C12H16N2O2 (1091632-54-0) + 1,4-bis(dodecyloxy)-2,5-diiodobenzene (145483-66-5) → 1,1'-hexyl-6,6'-[(1,4-bis(dodecyloxy)-2,5-phenylene)diethynyl]bisuracil (1290140-53-2)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In tetrahydrofuran; for 12h; Inert atmosphere;

DOI:10.1039/c3nj01606d

Reference yield:

1,4-bis-dodecyloxy-benzene (3230-09-9) → 1,1'-hexyl-6,6'-[(1,4-bis(dodecyloxy)-2,5-phenylene)diethynyl]bisuracil (1290140-53-2)

Guidance literature:

Multi-step reaction with 4 steps

1: mercury(II) diacetate; iodine / dichloromethane / 12 h / 20 °C

2: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

3: methanol; potassium hydroxide / tetrahydrofuran; water / 1 h / 20 °C

4: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

With methanol; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; mercury(II) diacetate; iodine; triethylamine; potassium hydroxide; In tetrahydrofuran; dichloromethane; water; 2: Sonogashira coupling / 4: Sonogashira coupling;

DOI:10.1021/ja2011516

upstream raw materials:

1-hexyl-6-iodo-2,4(1H,3H)-pyrimidinedione

1,4-bis(dodecyloxy)-2,5-diethynylbenzene

1,4-bis-dodecyloxy-benzene

1-dodecylbromide

Refernces

• 1、 Llanes-Pallas, Anna,Yoosaf,Traboulsi, Hassan,Mohanraj, John,Seldrum, Thomas,Dumont, Jacques,Minoia, Andrea,Lazzaroni, Roberto,Armaroli, Nicola,Bonifazi, Davide. "Modular engineering of H-bonded supramolecular polymers for reversible functionalization of carbon nanotubes". supporting information; experimental part. p. 15412 - 15424. Retrieved 2011/11/12.