2-Bromo-3-decylthiophene

Base Information

• Chemical Name: 2-Bromo-3-decylthiophene
• CAS No.: 144012-09-9
• Molecular Formula: C₁₄H₂₃BrS
• Molecular Weight: 303.307
• Hs Code.: 2934999090
• Mol file: 144012-09-9.mol

Synonyms:3-Decyl-2-bromothiophene;

Chemical Property of 2-Bromo-3-decylthiophene

Chemical Property:

• Refractive Index: 1.5120 to 1.5160
• Boiling Point: 339.626 °C at 760 mmHg
• Flash Point: 159.201 °C
• PSA: 28.24000
• Density: 1.167 g/cm³
• LogP: 6.19380
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

99% ^*data from raw suppliers

2-Bromo-3-decylthiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Bromo-3-decylthiophene

There total 3 articles about 2-Bromo-3-decylthiophene 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: 91.0%

3-decylthiophene (65016-55-9,110851-65-5) → 2-bromo-3-decylthiophene (144012-09-9)

Guidance literature:

With N-Bromosuccinimide; In tetrahydrofuran; at 20 ℃; for 15h;

DOI:10.1002/anie.200903247

Reference yield:

n-decyl magnesium bromide (17049-50-2) → 2-bromo-3-decylthiophene (144012-09-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / diethyl ether / 20 - 60 °C / Inert atmosphere

2: N-Bromosuccinimide / chloroform; acetic acid / 2 h / 20 °C / Inert atmosphere; Darkness

With N-Bromosuccinimide; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In diethyl ether; chloroform; acetic acid;

DOI:10.1021/ja107678m

Reference yield:

1-bromo dodecane (112-29-8) → 2-bromo-3-decylthiophene (144012-09-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: magnesium / tetrahydrofuran / Reflux

1.2: Reflux; Inert atmosphere

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

With N-Bromosuccinimide; magnesium; In tetrahydrofuran; N,N-dimethyl-formamide; 1.2: Kumada coupling reaction;

DOI:10.1039/c0jm02359k

upstream raw materials:

3-decylthiophene

n-decyl magnesium bromide

1-bromo dodecane

Downstream raw materials:

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

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

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

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

Refernces

• 1、 Wang, Ming,Wang, Hengbin,Ford, Michael,Yuan, Jianyu,Mai, Cheng-Kang,Fronk, Stephanie,Bazan, Guillermo C.. "Influence of molecular structure on the performance of low: V oc loss polymer solar cells". . p. 15232 - 15239. Retrieved 2016/10/13.
• 2、 Quinton, Cassandre,Alain-Rizzo, Valérie,Dumas-Verdes, Cécile,Clavier, Gilles,Vignau, Laurence,Audebert, Pierre. "Triphenylamine/tetrazine based π-conjugated systems as molecular donors for organic solar cells". . p. 9700 - 9713. Retrieved 2015/12/01.