5,5''-dibromo-3,3''-didecyl-2,2':5',2''-terthiophene

Base Information

• Chemical Name: 5,5''-dibromo-3,3''-didecyl-2,2':5',2''-terthiophene
• CAS No.: 1264297-33-7
• Molecular Formula: C₃₂H₄₆Br₂S₃
• Molecular Weight: 686.723
• Mol file: 1264297-33-7.mol

Synonyms:

Chemical Property of 5,5''-dibromo-3,3''-didecyl-2,2':5',2''-terthiophene

Chemical Property:

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,5''-dibromo-3,3''-didecyl-2,2':5',2''-terthiophene

There total 4 articles about 5,5''-dibromo-3,3''-didecyl-2,2':5',2''-terthiophene 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: 74.0%

3,3''-didecyl-2,2':5',2''-terthiophene (400713-59-9) → 5,5''-dibromo-3,3''-didecyl-2,2':5',2''-terthiophene (1264297-33-7)

Guidance literature:

With N-Bromosuccinimide; In tetrahydrofuran; at 0 - 20 ℃; Darkness;

DOI:10.1039/c0jm02359k

Reference yield:

1-bromo dodecane (112-29-8) → 5,5''-dibromo-3,3''-didecyl-2,2':5',2''-terthiophene (1264297-33-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: magnesium / tetrahydrofuran / Reflux

1.2: Reflux; Inert atmosphere

2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0 °C

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide; toluene / 16 h / 110 °C / Inert atmosphere

4.1: N-Bromosuccinimide / tetrahydrofuran / 0 - 20 °C / Darkness

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; magnesium; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 1.2: Kumada coupling reaction / 3.1: Stille coupling;

DOI:10.1039/c0jm02359k

Reference yield:

3-decylthiophene (65016-55-9,110851-65-5) → 5,5''-dibromo-3,3''-didecyl-2,2':5',2''-terthiophene (1264297-33-7)

Guidance literature:

Multi-step reaction with 3 steps

1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0 °C

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide; toluene / 16 h / 110 °C / Inert atmosphere

3: N-Bromosuccinimide / tetrahydrofuran / 0 - 20 °C / Darkness

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 2: Stille coupling;

DOI:10.1039/c0jm02359k

upstream raw materials:

3,3''-didecyl-2,2':5',2''-terthiophene

1-bromo dodecane

3-decylthiophene

2-bromo-3-decylthiophene

Refernces

• 1、 Brouwer, Frank,Alma, Jan,Valkenier, Hennie,Voortman, Thomas P.,Hillebrand, Jorrit,Chiechi, Ryan C.,Hummelen, Jan C.. "Using bis(pinacolato)diboron to improve the quality of regioregular conjugated co-polymers". experimental part. p. 1582 - 1592. Retrieved 2011/10/02.