4,8-bis(4-decylphenylethynyl)benzo[1,2-b:4,5-b']dithiophene

Base Information

• Chemical Name: 4,8-bis(4-decylphenylethynyl)benzo[1,2-b:4,5-b']dithiophene
• CAS No.: 1246263-85-3
• Molecular Formula: C₄₆H₅₄S₂
• Molecular Weight: 671.067
• Mol file: 1246263-85-3.mol

Synonyms:4,8-bis(4-decylphenylethynyl)benzo[1,2-b:4,5-b']dithiophene

Chemical Property of 4,8-bis(4-decylphenylethynyl)benzo[1,2-b:4,5-b']dithiophene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,8-bis(4-decylphenylethynyl)benzo[1,2-b:4,5-b']dithiophene

There total 6 articles about 4,8-bis(4-decylphenylethynyl)benzo[1,2-b:4,5-b']dithiophene 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: 52.0%

4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione (32281-36-0) + 1-decyl-4-ethynylbenzene (126708-45-0) → 4,8-bis(4-decylphenylethynyl)benzo[1,2-b:4,5-b']dithiophene (1246263-85-3)

Guidance literature:

1-decyl-4-ethynylbenzene; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h; Inert atmosphere;

4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione; In tetrahydrofuran; hexane; for 1h; Inert atmosphere; Reflux;

With hydrogenchloride; tin(II) chloride dihdyrate; In tetrahydrofuran; hexane; water; for 2h; Inert atmosphere; Reflux;

DOI:10.1021/ma101709h

Reference yield:

bromobenzene (108-86-1,52753-63-6) → 4,8-bis(4-decylphenylethynyl)benzo[1,2-b:4,5-b']dithiophene (1246263-85-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: aluminum (III) chloride / 1 h / 60 °C / Inert atmosphere

2.1: hydrazine hydrate; potassium hydroxide / octanol / 3 h / Reflux; Inert atmosphere

3.1: copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine / 50 - 80 °C / Inert atmosphere

4.1: potassium hydroxide / methanol; dichloromethane / 1 h / 20 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere

5.2: 1 h / Inert atmosphere; Reflux

5.3: 2 h / Inert atmosphere; Reflux

With aluminum (III) chloride; copper(l) iodide; n-butyllithium; trans-bis(triphenylphosphine)palladium dichloride; hydrazine hydrate; triethylamine; potassium hydroxide; In tetrahydrofuran; methanol; octanol; hexane; dichloromethane; 1.1: Friedel Crafts acylation / 2.1: Wolf-Kishner reaction / 3.1: Sonogashira coupling;

DOI:10.1021/ma101709h

Reference yield:

1-bromo-4-n-decyl benzene (106418-67-1) → 4,8-bis(4-decylphenylethynyl)benzo[1,2-b:4,5-b']dithiophene (1246263-85-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine / 50 - 80 °C / Inert atmosphere

2.1: potassium hydroxide / methanol; dichloromethane / 1 h / 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere

3.2: 1 h / Inert atmosphere; Reflux

3.3: 2 h / Inert atmosphere; Reflux

With copper(l) iodide; n-butyllithium; trans-bis(triphenylphosphine)palladium dichloride; triethylamine; potassium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; 1.1: Sonogashira coupling;

DOI:10.1021/ma101709h

upstream raw materials:

bromobenzene

(2-(4-decylphenyl)ethynyl)trimethylsilane

4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione

1-decyl-4-ethynylbenzene

Downstream raw materials:

2,6-dibromo-4,8-bis(4-decylphenylethynyl)benzo-[1,2-b:4,5-b']dithiophene

Refernces