4,7-dibroMo-5,6-dinitrobenzo[c][1,2,5]thiadiazole

Base Information

• Chemical Name: 4,7-dibroMo-5,6-dinitrobenzo[c][1,2,5]thiadiazole
• CAS No.: 76186-72-6
• Molecular Formula: C6Br2N4O4S
• Molecular Weight: 383.964
• Mol file: 76186-72-6.mol

Synonyms:4,7-Dibromo-5,6-dinitro-benzo[1,2,5]thiadiazole;4,7-dibromo-5,6-dinitrobenzo[c][1,2,5]thiadiazole;4,7-dibromo-5,6-dinitro-2,1,3-benzothiadiazole;4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole;4,7-dibromo-5,6-dinitro-2,1,3-benthiadiazole;4,7-dibromo-5,6-dinitrobenzo[c]-[1,2,5]thiadiazole;4,7-dibromo-5,6-dinitrobenzothiadiazole;4,7-dibromo-5,6-dinitrobenzo[1,2,5]thiadiazole;

Chemical Property of 4,7-dibroMo-5,6-dinitrobenzo[c][1,2,5]thiadiazole

Chemical Property:

• Melting Point: 198 °C(Solv: ethanol (64-17-5))
• Boiling Point: 418.338 °C at 760 mmHg
• PKA: -8.74±0.50(Predicted)
• Flash Point: 206.804 °C
• PSA: 145.66000
• Density: 2.469 g/cm³
• LogP: 4.07910
• Storage Temp.: 2-8°C

Purity/Quality:

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

2,1,3-Benzothiadiazole,4,7-dibromo-5,6-dinitro- 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4,7-Dibromo-5,6-dintiro-2,1,3-benzothiadiazole can be incorporated in light-emitting diodes producing near-IR sensitivity.

Technology Process of 4,7-dibroMo-5,6-dinitrobenzo[c][1,2,5]thiadiazole

There total 3 articles about 4,7-dibroMo-5,6-dinitrobenzo[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: 95.0%

4,7-dibromobenzo[c][1,2,5]thiadiazole (15155-41-6) → 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6)

Guidance literature:

With sulfuric acid; nitric acid; In toluene; at 20 ℃; for 20h;

Reference yield:

benzo[1,2,5]thiadiazole (273-13-2,22706-22-5) → 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. HBr; Br₂ / 130 °C

2: CF₃CO₂H; HNO₃ / CH₂Cl₂

With hydrogen bromide; bromine; nitric acid; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ja040243h

Reference yield:

1,2-diamino-benzene (95-54-5) → 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride; triethylamine / dichloromethane

2: hydrogen bromide; bromine / water

3: sulfuric acid; nitric acid

With thionyl chloride; sulfuric acid; hydrogen bromide; bromine; nitric acid; triethylamine; In dichloromethane; water;

DOI:10.1039/c0jm03436c

upstream raw materials:

4,7-dibromobenzo[c][1,2,5]thiadiazole

benzo[1,2,5]thiadiazole

1,2-diamino-benzene

Downstream raw materials:

5,6-dinitro-4,7-diphenylbenzo[c][1,2,5]thiadiazole

C₃₂H₁₄N₈O₄S₄

4,10-bis(thiophen-2-yl)-7-[4-(heptadecan-9-yloxy)-phenyl]-6H-[1,2,5]thiadiazole[3,4-g]benzoimidazole

4,10-bis(5-bromothiophen-2-yl)-7-[4-(heptadecan-9-yloxy)-phenyl]-6H-[1,2,5]thiadiazole[3,4-g]benzoimidazole

Refernces

• 1、 Hu, Benlin,Li, Miaomiao,Chen, Wangqiao,Wan, Xiangjian,Chen, Yongsheng,Zhang, Qichun. "Novel donor-acceptor polymers based on 7-perfluorophenyl-6H-[1,2,5]thiadiazole[3,4-g]benzoimidazole for bulk heterojunction solar cells". . p. 50137 - 50145. Retrieved 2015.
• 2、 Schleper, A. Lennart,Voll, Constantin-Christian A.,Engelhart, Jens U.,Swager, Timothy M.. "Iptycene-Containing Azaacenes with Tunable Luminescence". . p. 2783 - 2789. Retrieved 2017.
• 3、 -. "Ester-substituted heterocyclic aromatic conjugated skeleton and polymer material and application thereof". Paragraph 0033; 0051; 0054-0055. . Retrieved 2021/08/19.
• 4、 Cheng, Zijin,Zhang, Tian,Wang, Weili,Shen, Qing,Hong, Ying,Shao, Jinjun,Xie, Xiaoji,Fei, Zhenghao,Dong, Xiaochen. "D-A-D structured selenadiazolesbenzothiadiazole-based near-infrared dye for enhanced photoacoustic imaging and photothermal cancer therapy". supporting information. p. 1582 - 1587. Retrieved 2021/03/08.