4-bromo-7-(2,2-dicyanovinyl)-2,1,3-benzothiadiazole

Base Information

• Chemical Name: 4-bromo-7-(2,2-dicyanovinyl)-2,1,3-benzothiadiazole
• CAS No.: 1335150-10-1
• Molecular Formula: C10H3BrN4S
• Molecular Weight: 291.131
• Mol file: 1335150-10-1.mol

Synonyms:4-bromo-7-(2,2-dicyanovinyl)-2,1,3-benzothiadiazole

Chemical Property of 4-bromo-7-(2,2-dicyanovinyl)-2,1,3-benzothiadiazole

Chemical Property:

• Melting Point: 187.0 to 191.0 °C
• Boiling Point: 450.0±40.0 °C(Predicted)
• PKA: -3.28±0.50(Predicted)
• PSA: 101.60000
• Density: 1.822±0.06 g/cm3(Predicted)
• LogP: 2.88436

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-[(7-Bromo-2,1,3-benzothiadiazol-4-yl)methylene]propanedinitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-bromo-7-(2,2-dicyanovinyl)-2,1,3-benzothiadiazole

There total 3 articles about 4-bromo-7-(2,2-dicyanovinyl)-2,1,3-benzothiadiazole 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: 67.0%

7-bromobenzo[c][1,2,5]thiadiazole-4-carboxaldehyde (1071224-34-4) + malononitrile (109-77-3) → 2-((7-bromobenzo[c][1,2,5]thiadiazol-4-yl)methylene)malononitrile (1335150-10-1)

Guidance literature:

With aluminum oxide; In toluene; at 70 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ja205126t

Reference yield:

4-bromo-7-dibromomethyl-2,1,3-benzothiadiazole (1239277-96-3) → 2-((7-bromobenzo[c][1,2,5]thiadiazol-4-yl)methylene)malononitrile (1335150-10-1)

Guidance literature:

Multi-step reaction with 2 steps

1: silver nitrate / water; acetonitrile / 2 h / Reflux; Inert atmosphere

2: aluminum oxide / toluene / 2 h / 70 °C / Inert atmosphere

With aluminum oxide; silver nitrate; In water; toluene; acetonitrile; 2: Knoevenagel condensation;

DOI:10.1021/ja205126t

Reference yield:

4-bromo-7-methylbenzo[c][1,2,5]thiadiazole (2255-80-3) → 2-((7-bromobenzo[c][1,2,5]thiadiazol-4-yl)methylene)malononitrile (1335150-10-1)

Guidance literature:

Multi-step reaction with 3 steps

1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chlorobenzene / 4 h / 80 °C / Inert atmosphere

2: silver nitrate / water; acetonitrile / 2 h / Reflux; Inert atmosphere

3: aluminum oxide / toluene / 2 h / 70 °C / Inert atmosphere

With aluminum oxide; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); silver nitrate; In water; chlorobenzene; toluene; acetonitrile; 3: Knoevenagel condensation;

DOI:10.1021/ja205126t

upstream raw materials:

4-bromo-7-dibromomethyl-2,1,3-benzothiadiazole

7-bromobenzo[c][1,2,5]thiadiazole-4-carboxaldehyde

malononitrile

4-bromo-7-methylbenzo[c][1,2,5]thiadiazole

Downstream raw materials:

2-{[7-(5-(N,N-di-p-tolyl)aminothiophen-2-yl)-2,1,3-benzothiadiazol-4-yl]methylene}malononitrile

2-{[7-(2-fluoro-4-(N,N-di-p-tolyl)aminophenyl)-2,1,3-benzothiadiazol-4-yl]methylene}malononitrile

2-{[7-(4-(N,N-diphenyl)aminophenyl)-2,1,3-benzothiadiazol-4-yl]methylene}malononitrile

2-{[7-(5-(N,N-diphenyl)aminothiophen-2-yl)-2,1,3-benzothiadiazol-4-yl]methylene}malononitrile

Refernces

• 1、 Lin, Li-Yen,Chen, Yi-Hong,Huang, Zheng-Yu,Lin, Hao-Wu,Chou, Shu-Hua,Lin, Francis,Chen, Chang-Wen,Liu, Yi-Hung,Wong, Ken-Tsung. "A low-energy-gap organic dye for high-performance small-molecule organic solar cells". . p. 15822 - 15825. Retrieved 2011/11/13.