4,7-bis(5-bromothiophen-2-yl)-5,6-bis(dodecyloxy)benzo[c][1,2,5]thiadiazole

Base Information

• Chemical Name: 4,7-bis(5-bromothiophen-2-yl)-5,6-bis(dodecyloxy)benzo[c][1,2,5]thiadiazole
• CAS No.: 1334686-71-3
• Molecular Formula: C₃₈H₅₄Br₂N₂O₂S₃
• Molecular Weight: 826.865
• Mol file: 1334686-71-3.mol

Synonyms:

Chemical Property of 4,7-bis(5-bromothiophen-2-yl)-5,6-bis(dodecyloxy)benzo[c][1,2,5]thiadiazole

Chemical Property:

Purity/Quality:

98% purity ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,7-bis(5-bromothiophen-2-yl)-5,6-bis(dodecyloxy)benzo[c][1,2,5]thiadiazole

There total 11 articles about 4,7-bis(5-bromothiophen-2-yl)-5,6-bis(dodecyloxy)benzo[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: 97.0%

5,6-bis(dodecyloxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]-thiadiazole (1334686-70-2) → 4,7-bis(5-bromothiophen-2-yl)-5,6-bis(dodecyloxy)benzo[c][1,2,5]thiadiazole (1334686-71-3)

Guidance literature:

With N-Bromosuccinimide; In tetrahydrofuran; for 18h; Inert atmosphere; Cooling with ice;

DOI:10.1002/pola.24879

Reference yield:

1,2-bisdodecyloxybenzene (42244-53-1) → 4,7-bis(5-bromothiophen-2-yl)-5,6-bis(dodecyloxy)benzo[c][1,2,5]thiadiazole (1334686-71-3)

Guidance literature:

Multi-step reaction with 6 steps

1: nitric acid / 20 °C / Cooling with ice; Inert atmosphere

2: hydrogen bromide; tin(II) bromide / ethanol / 18 h / 100 °C / Inert atmosphere

3: pyridine; sulfurous dibromide / chloroform / 70 °C / Inert atmosphere; Cooling with ice

4: bromine; acetic acid / dichloromethane / 48 h / 40 °C / Inert atmosphere; Darkness

5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; water / 72 h / 80 °C / Inert atmosphere; Darkness

6: N-Bromosuccinimide / tetrahydrofuran / 18 h / Inert atmosphere; Cooling with ice

With pyridine; N-Bromosuccinimide; sulfurous dibromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen bromide; bromine; nitric acid; tin(II) bromide; sodium carbonate; acetic acid; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; 5: Suzuki coupling;

DOI:10.1002/pola.24879

Reference yield:

benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) → 4,7-bis(5-bromothiophen-2-yl)-5,6-bis(dodecyloxy)benzo[c][1,2,5]thiadiazole (1334686-71-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium hydroxide / ethanol / 0.5 h / 60 °C / Inert atmosphere

1.2: 60 °C / Inert atmosphere

2.1: nitric acid / 20 °C / Cooling with ice; Inert atmosphere

3.1: hydrogen bromide; tin(II) bromide / ethanol / 18 h / 100 °C / Inert atmosphere

4.1: pyridine; sulfurous dibromide / chloroform / 70 °C / Inert atmosphere; Cooling with ice

5.1: bromine; acetic acid / dichloromethane / 48 h / 40 °C / Inert atmosphere; Darkness

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; water / 72 h / 80 °C / Inert atmosphere; Darkness

7.1: N-Bromosuccinimide / tetrahydrofuran / 18 h / Inert atmosphere; Cooling with ice

With pyridine; N-Bromosuccinimide; sulfurous dibromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen bromide; bromine; nitric acid; tin(II) bromide; sodium carbonate; acetic acid; potassium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; 6.1: Suzuki coupling;

DOI:10.1002/pola.24879

upstream raw materials:

4,7-dibromo-5,6-bis(dodecyloxy)benzo[c][1,2,5]thiadiazole

5,6-bis(dodecyloxy)benzo[c][1,2,5]thiadiazole

5,6-bis(dodecyloxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]-thiadiazole

1,2-bisdodecyloxybenzene