4,7-Bis(5-broMo-4-octylthiophen-2-yl)-5,6-difluorobenzo[c][1,2,5] thiadiazole

Base Information

• Chemical Name: 4,7-Bis(5-broMo-4-octylthiophen-2-yl)-5,6-difluorobenzo[c][1,2,5] thiadiazole
• CAS No.: 1283598-36-6
• Molecular Formula: C30H36Br2F2N2S3
• Molecular Weight: 718.632
• Mol file: 1283598-36-6.mol

Synonyms:4,7-Bis(5-broMo-4-octylthiophen-2-yl)-5,6-difluorobenzo[c][1,2,5] thiadiazole

Chemical Property of 4,7-Bis(5-broMo-4-octylthiophen-2-yl)-5,6-difluorobenzo[c][1,2,5] thiadiazole

Chemical Property:

• PSA: 110.50000
• LogP: 12.75750

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4,7-Bis(5-broMo-4-octylthiophen-2-yl)-5,6-difluorobenzo[c][1,2,5] thiadiazole

There total 10 articles about 4,7-Bis(5-broMo-4-octylthiophen-2-yl)-5,6-difluorobenzo[c][1,2,5] thiadiazole 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: 98.0%

5,6-difluoro-4,7-bis(4-octylthiophen-2-yl)benzo[c][1,2,5]thiadiazole (1283598-35-5) → 4,7-bis(5-bromo-4-octylthiophen-2-yl)-5,6-difluorobenzo[c][1,2,5]thiadiazole (1283598-36-6)

Guidance literature:

With N-Bromosuccinimide; silica gel; In chloroform; at 20 ℃; for 3.5h;

DOI:10.1039/c0jm04166a

Reference yield:

2-amino-4,5-difluoroaniline (76179-40-3) → 4,7-bis(5-bromo-4-octylthiophen-2-yl)-5,6-difluorobenzo[c][1,2,5]thiadiazole (1283598-36-6)

Guidance literature:

Multi-step reaction with 4 steps

1: aniline; thionyl chloride / toluene / 0 - 100 °C / Inert atmosphere

2: N-iodo-succinimide; acetic acid; sulfuric acid / 24 h / 20 °C / Inert atmosphere

3: sodium hydrogencarbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tris-(o-tolyl)phosphine / tetrahydrofuran; water / 72 h / 90 °C / Inert atmosphere

4: bromine / dichloromethane / 0.02 h / 20 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-iodo-succinimide; thionyl chloride; sulfuric acid; bromine; sodium hydrogencarbonate; acetic acid; aniline; tris-(o-tolyl)phosphine; In tetrahydrofuran; dichloromethane; water; toluene; 3: |Suzuki-Miyaura Coupling;

DOI:10.1039/c4tc00340c

Reference yield:

5,6‐difluoro‐2,1,3‐benzothiadiazole (1293389-28-2) → 4,7-bis(5-bromo-4-octylthiophen-2-yl)-5,6-difluorobenzo[c][1,2,5]thiadiazole (1283598-36-6)

Guidance literature:

Multi-step reaction with 3 steps

1: N-iodo-succinimide; acetic acid; sulfuric acid / 24 h / 20 °C / Inert atmosphere

2: sodium hydrogencarbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tris-(o-tolyl)phosphine / tetrahydrofuran; water / 72 h / 90 °C / Inert atmosphere

3: bromine / dichloromethane / 0.02 h / 20 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-iodo-succinimide; sulfuric acid; bromine; sodium hydrogencarbonate; acetic acid; tris-(o-tolyl)phosphine; In tetrahydrofuran; dichloromethane; water; 2: |Suzuki-Miyaura Coupling;

DOI:10.1039/c4tc00340c

upstream raw materials:

1,4-dibromo-2,3-difluoro-benzene

1,4-dibromo-2,3-difluoro-5,6-dinitrobenzene

1,4-bis(4-octyl-2-thienyl)-2,3-difluoro-5,6-dinitrobenzene

1,4-bis(4-octyl-2-thienyl)-2,3-difluoro-5,6-diaminobenzene

Refernces

• 1、 Deng, Zhiqiang,Wu, Feiyan,Chen, Lie,Chen, Yiwang. "Novel photovoltaic donor 1-acceptor-donor 2-acceptor terpolymers with tunable energy levels based on a difluorinated benzothiadiazole acceptor". . p. 12087 - 12093. Retrieved 2015/02/19.
• 2、 -. "FLUORINATED MONOMERS, OLIGOMERS AND POLYMERS FOR USE IN ORGANIC ELECTRONIC DEVICES". Page/Page column 9-10. . Retrieved 2011/06/19.