4,7-DIBROMO-2,1,3-BENZOTHIADIAZOLE

Base Information

• Chemical Name: 4,7-DIBROMO-2,1,3-BENZOTHIADIAZOLE
• CAS No.: 15155-41-6
• Molecular Formula: C6H2Br2N2S
• Molecular Weight: 293.969
• Hs Code.: 29349990
• Mol file: 15155-41-6.mol

Synonyms:4,7-Dibromo-1,2,3-benzothiadiazole;4,7-Dibromobenzo[1,2,5]thiadiazole;4,7-Dibromobenzo[c][1,2,5]thiadiazole;4,7-Dibromobenzothiadiazole;4,7-dibromo-2,1,3-benzothiadiazole;2,1,3-benzothiadiazole, 4,7-dibromo-;

Chemical Property of 4,7-DIBROMO-2,1,3-BENZOTHIADIAZOLE

Chemical Property:

• Appearance/Colour: pale yellow powder
• Vapor Pressure: 0.000405mmHg at 25°C
• Melting Point: 186-190 °C
• Refractive Index: 1.756
• Boiling Point: 326.6 °C at 760 mmHg
• PKA: -3.37±0.50(Predicted)
• Flash Point: 151.3 °C
• PSA: 54.02000
• Density: 2.229 g/cm³
• LogP: 3.21630
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Soluble in toluene.

Purity/Quality:

98% ^*data from raw suppliers

4,7-Dibromobenzo-2,1,3-thiadiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi; Xn
• Hazard Codes: Xn,Xi
• Statements: 22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Description: 4,7-Dibromo-2,1,3-benzothiadiazole is the building block or monomer for organic semiconductors synthesis in the application of light-emitting diodes and photovoltaic devices. Intermediate for the synthesis of i.e. PCDTBT and PCPDTBT.
• Uses: 4,7-Dibromo-2,1,3-benzothiadiazole is the building block or monomer for the synthesis of light-emitting diodes and conducting polymers for organic electronics. It is used as an intermediate for the synthesis of poly[N-9'-heptadecanyl-2,7-carbazole-alt-5,5-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] (PCDTBT) and poly[2,1,3-benzothiadiazole-4,7-diyl[4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene-2,6-diyl]] (PCPDTBT). This monomer is used in the synthesis of photoactive acceptor part in low band gap conjugated polymers and oligomers for high performance OPV devices

Technology Process of 4,7-DIBROMO-2,1,3-BENZOTHIADIAZOLE

There total 15 articles about 4,7-DIBROMO-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: 98.0%

benzo[1,2,5]thiadiazole (273-13-2,22706-22-5) → 4,7-dibromobenzo[c][1,2,5]thiadiazole (15155-41-6)

Guidance literature:

With hydrogen bromide; bromine; Inert atmosphere;

DOI:10.1016/j.polymer.2010.10.045

Reference yield: 89.0%

benzo[1,2,3]thiadiazole (273-77-8) → 4,7-dibromobenzo[c][1,2,5]thiadiazole (15155-41-6)

Guidance literature:

With hydrogen bromide; bromine; at 120 ℃; for 16h;

Reference yield: 87.0%

5,6-dimethylbenzo-2,1,3-thiadiazole (1887-60-1) → 4,7-dibromobenzo[c][1,2,5]thiadiazole (15155-41-6)

Guidance literature:

With hydrogen bromide; bromine; at 100 ℃; for 12h; Inert atmosphere;

DOI:10.1002/chem.201804261

upstream raw materials:

benzo[1,2,5]thiadiazole

7-bromo-benzo[1,2,5]thiadiazole-4-sulfonic acid

1,2-diamino-benzene

4-Bromo-benzo[1,2,5]thiadiazole

Downstream raw materials:

4,7-bis(4-trimethylsilylphenyl)-2,1,3-benzothiadiazole

4,7-diphenyl-2,1,3-benzothiadiazole

4,7-bis-(4-hexyl-thiophen-2-yl)-benzo[1,2,5]thiadiazole

4,4'-(benzo[c][1,2,5]thiadiazole-4,7-diyl)dibenzonitrile

Refernces

• 1、 Damiani, Adriani P.,Rohr, Paula,Westrup, José L.,Duarte, Rodrigo C.,Longaretti, Luiza M.,Da Rocha, Bruna M.,Strapazzon, Giulia,Venturini, Lara C.,Souza, Emanuel,Pich, Claus T.,Frizon, Tiago E. A.,De Andrade, Vanessa M.,Rodembusch, Fabiano S.,Dal-Bo, Alexandre G.. "Synthesis, DNA interaction and genotoxic evaluation of a photoactive benzothiadiazole with potential application in photovoltaic paint". . p. 1388 - 1399. Retrieved 2018.
• 2、 Witker, David,Reynolds, John R.. "Soluble variable color carbazole-containing electrochromic polymers". . p. 7636 - 7644. Retrieved 2005.
• 3、 Cevher, Sevki Can,Hizalan, Gonul,Temiz, Cansel,Udum, Yasemin Arslan,Toppare, Levent,Cirpan, Ali. "Effect of substituent groups on quinoxaline-based random copolymers on the optoelectronic and photovoltaic properties". . p. 208 - 216. Retrieved 2016.
• 4、 Westrup, José Luiz,Oenning, Leonardo Werncke,Da Silva Paula, Marcos Marques,Da Costa Duarte, Rodrigo,Rodembusch, Fabiano Severo,Frizon, Tiago Elias Allievi,Da Silva, Luciano,Dal-Bó, Alexandre Gon?alves. "New photoactive D-π-A-π-D benzothiadiazole derivative: Synthesis, thermal and photophysical properties". . p. 209 - 217. Retrieved 2016.
• 5、 Rietsch, Philipp,Sobottka, Sebastian,Hoffmann, Katrin,Popov, Alexey A.,Hildebrandt, Pascal,Sarkar, Biprajit,Resch-Genger, Ute,Eigler, Siegfried. "Between Aromatic and Quinoid Structure: A Symmetrical UV to Vis/NIR Benzothiadiazole Redox Switch". . p. 17361 - 17365. Retrieved 2020.
• 6、 Jana, Ajay Kumar,Natarajan, Srinivasan. "Fluorescent metal-organic frameworks for selective sensing of toxic cations (Tl3+, Hg2+) and highly oxidizing anions ((CrO4)2?, (Cr2O7)2?, (MnO4)?)". . p. 1153 - 1163. Retrieved 2017.
• 7、 Jiu, Yuanda,Wang, Jianyun,Liu, Chengfang,Lai, Wenyong,Zhao, Lingling,Li, Xiangchun,Jiang, Yi,Xu, Weidong,Zhang, Xinwen,Huang, Wei. "White Electroluminescence with Simultaneous Three-Color Emission from a Four-Armed Star-Shaped Single-Polymer System". . p. 873 - 880. Retrieved 2015.
• 8、 Bhanvadia, Viraj J.,Patel, Heta A.,Sharma, Neha N.,Patel, Arun L.. "Synthesis, photophysical, electrochemical and single-crystal x-ray diffraction study of (Z)-2-phenyl-3-(5-(4-(thiophen-2-yl)benzo[c][1,2,5]thiadiazol-7-yl)thiophen-2-yl)acrylonitrile". . p. 1052 - 1061. Retrieved 2016.
• 9、 Soylemez, Saniye,Hacioglu, Serife O.,Uzun, Sema Demirci,Toppare, Levent. "A low band gap benzimidazole derivative and its copolymer with 3,4-ethylenedioxythiophene for electrochemical studies". . p. H6 - H14. Retrieved 2015.
• 10、 Baggi, Giorgio,Loeb, Stephen J.. "Rotationally Active Ligands: Dialing-Up the Co-conformations of a [2]Rotaxane for Metal Ion Binding". . p. 12533 - 12537. Retrieved 2016.