2,1,3-Benzothiadiazole

Organic bicyclic chemical 2,1,3-Benzothiadiazole 2,1,3-Benzothiadiazole.svg 2,1,3-Benzothiadiazole Piazthiole Benzisothiadiazole Benzo[1,2,5]thiadiazole 67502 273-13-2 correct FDA 8FTH8AJA9H 205-985-2 60826 DTXSID3059767 1S/C6H4N2S/c1-2-4-6-5(3-1)7-9-8-6/h1-4H PDQRQJVPEFGVRK-UHFFFAOYSA-N C1=CC2=NSN=C2C=C1 6 4 2 1 54.0 203.0 1,2,3-Benzothiadiazole 07 Warning 315 319 335 261 264 271 280 302+352 304+340 305+351+338 312 321 332+313 337+313 362 403+233 405 501 2,1,3-Benzothiadiazole is a bicyclic molecule composed of a benzene ring that is fused to a 1,2,5-thiadiazole. Preparation and structure 2,1,3-Benzothiadiazole has been known since the 19th century. It is readily prepared in at least 85% yield from o-phenylenediamine by reaction with two equivalents of thionyl chloride in pyridine. The by-products are sulfur dioxide and HCl.10.1007/BF00468340 Research on 2,1,3-thia- and selenadiazole 1969 Pesin V. G. Sergeev V. A. Chemistry of Heterocyclic Compounds 3 5 662–666 98830770 400px There are a number of alternative methods used to make this heterocycle and these have been reviewed.10.1055/sos-SD-013-00458 Product Class 11: 1,2,5-Thiadiazoles and Related Compounds Category 2, Hetarenes and Related Ring Systems 2004 978-3-13-112281-0 Storr Gilchrist 10.1055/s-0039-1690679 Recent Developments in the Synthesis of 1,2,5-Thiadiazoles and 2,1,3-Benzothiadiazoles 2019 Rakitin Oleg A. Synthesis 51 23 4338–4347 204128866 The crystal structure of the compound was determined in 1951, when it had the common name piazthiol(e).Luzzati Z.Z. Structure cristalline de piasélénol, piazthiol et benzofurazane Acta Crystallographica 1951 4 3 193–200 10.1107/S0365110X51000702 1951AcCry...4..193L Reactions The extent of the aromaticity of the compound was examined by a study of its proton NMR spectrum and comparison with naphthalene, which allowed the conclusion that it and related oxygen and selenium heterocycles did behave as 10-electron systems in which the 2-heteroatom contributed its lone pair to the ring current, in accordance with Hückel's rule.10.1007/BF00755265 https://link.springer.com/content/pdf/10.1007/BF00755265.pdf Studies in the field of aromatic heterocycles 1970 Fedin E. I. Todres Z. V. Chemistry of Heterocyclic Compounds 4 3 308–313 91864834 As a result, 2,1,3-benzothiadiazole undergoes the standard chemistry of aromatic compounds, for example readily forming nitro and chloro derivatives.10.1007/BF00944264 Researches on 2,1,3-thia-and selenadiazole 1969 Pesin V. G. d'Yachenko E. K. Chemistry of Heterocyclic Compounds 3 68–70 100997583 The chemistry of this heterocycle and its simple derivatives has been reviewed.978-3-13-181244-5 Houben-Weyl Methods of Organic Chemistry Vol. E 8d, 4th Edition Supplement: Hetarenes III (Five-Membered Rings with Two and More Heteroatoms in the Ring System) - Part 4 14 May 2014 Georg Thieme Verlag Under reducing conditions, 2,1,3-benzothiadiazoles can be converted back to the 1,2-diaminobenzene compounds from which they were prepared. This can be a useful way to protect a pair of reactive amino groups while other transformations are performed in the benzene ring to which they are attached.Neto Brenno A. D. Lapis Alexandre A. M. da Silva Júnior Eufrânio N. Dupont Jairton January 2013 2,1,3-Benzothiadiazole and Derivatives: Synthesis, Properties, Reactions, and Applications in Light Technology of Small Molecules European Journal of Organic Chemistry 2013 2 228–255 10.1002/ejoc.201201161 Bromination of 2,1,3-Benzothiadiazole is commonly performed to synthesize 4,7-dibromo-2,1,3-benzothiadiazole. This derivative is extensively used as building block in the design and synthesis of larger molecules and conductive polymers via Suzuki-Miyaura cross-coupling reactions.Huang Jian Niu Yuhua Yang Wei Mo Yueqi Yuan Ming Cao Yong 2002-07-01 Novel Electroluminescent Polymers Derived from Carbazole and Benzothiadiazole https://pubs.acs.org/doi/10.1021/ma0255130 Macromolecules en 35 16 6080–6082 10.1021/ma0255130 2002MaMol..35.6080H 0024-9297 subscription center|frameless|Typical bromination conditions used in the synthesis of ,7-dibromo-2,1,3-benzothiadiazole Derivatives 2,1,3-Benzothiadiazole derivatives containing carbazole units have been found to be luminescent, with high emission intensity and quantum efficiency.Tao Yun-Mei Li Hong-Yan Xu Qiu-Lei Zhu Yu-Cheng Kang Ling-Chen Zheng You-Xuan Zuo Jing-Lin You Xiao-Zeng 2011 Synthesis and characterization of efficient luminescent materials based on 2,1,3-benzothiadiazole with carbazole moieties https://linkinghub.elsevier.com/retrieve/pii/S0379677911000348 Synthetic Metals en 161 9–10 718–723 10.1016/j.synthmet.2011.01.020 subscription Different π-extended molecular systems based on 2,1,3-benzothiadiazole have been built to study fundamental structure–property relationships. One example of this type of oligomer consist of extended thiophene building blocks as electron donors and 2,1,3-benzothiadiazole as electron aceptor. This oligomer was synthesized using a Sonogashira cross-coupling reaction and it showed low HOMO–LUMO gaps which could be interesting for organic semiconductor applications.Kitamura Chitoshi Saito Kakuya Ouchi Mikio Yoneda Akio Yamashita Yoshiro October 2002 Synthesis and Crystal Structure of 4,7-bis (2-thienylethynyl)-2,1,3-benzothiadiazole Journal of Chemical Research en 2002 10 511–513 10.3184/030823402103170565 1747-5198 free Asymmetric derivatives with diphenylamine donors, cyanoacrylic acid acceptors and thiophene linkers bridged by a 2,1,3-benzothiadiazole have been designed as organic dyes with improved charge separation propertiesVelusamy Marappan Justin Thomas K. R. Lin Jiann T. Hsu Ying-Chan Ho Kuo-Chuan 2005-05-01 Organic Dyes Incorporating Low-Band-Gap Chromophores for Dye-Sensitized Solar Cells https://pubs.acs.org/doi/10.1021/ol050417f Organic Letters en 7 10 1899–1902 10.1021/ol050417f 15876014 1523-7060 subscription when compared to classic cyanineEhret A. Stuhl L. Spitler M. T. 2001-10-01 Spectral Sensitization of TiO 2 Nanocrystalline Electrodes with Aggregated Cyanine Dyes https://pubs.acs.org/doi/10.1021/jp011952%2B The Journal of Physical Chemistry B en 105 41 9960–9965 10.1021/jp011952+ 1520-6106 subscription and hemicyanineYao Qiao-Hong Meng Fan-Shun Li Fu-You Tian He Huang Chun-Hui 2003-04-16 Photoelectric conversion properties of four novel carboxylated hemicyanine dyes on TiO2 electrode http://xlink.rsc.org/?DOI=b300083b Journal of Materials Chemistry 13 5 1048–1053 10.1039/b300083b subscription dyes. Applications 2,1,3-Benzothiadiazole has been of interest as a redox-active organic component in flow batteries owing to its favourable solubility, low reduction potential and fast electrochemical kinetics.10.1021/acsenergylett.7b00261 "Wine-Dark Sea" in an Organic Flow Battery: Storing Negative Charge in 2,1,3-Benzothiadiazole Radicals Leads to Improved Cyclability 2017 Duan Wentao Huang Jinhua Kowalski Jeffrey A. Shkrob Ilya A. Vijayakumar M. Walter Eric Pan Baofei Yang Zheng Milshtein Jarrod D. Li Bin Liao Chen Zhang Zhengcheng Wang Wei Liu Jun Moore Jeffery S. Brushett Fikile R. Zhang Lu Wei Xiaoliang ACS Energy Letters 2 5 1156–1161 Such properties in derivatives containing this heterocycle have made it of growing interest in dyestuffs,Frizon Tiago Elias Allievi Valdivia Martínez Julio César Westrup José Luiz Duarte Rodrigo da Costa Zapp Eduardo Domiciano Kelvin Guessi Rodembusch Fabiano Severo Dal-Bó Alexandre Gonçalves December 2016 2,1,3-Benzothiadiazole-based fluorophores. Synthesis, electrochemical, thermal and photophysical characterization Dyes and Pigments 135 26–35 10.1016/j.dyepig.2016.07.011 white light-emitting polymers,10.1007/978-3-642-14935-1_2 White-Emitting Polymers and Devices WOLEDs and Organic Photovoltaics Green Energy and Technology 2010 Wu Hongbin Ying Lei Yang Wei Cao Yong 37–78 978-3-642-14934-4 54914788 solar cells,10.1039/C6TC01860B free Benzothiadiazole and its π-extended, heteroannulated derivatives: Useful acceptor building blocks for high-performance donor–acceptor polymers in organic electronics 2016 Wang Yang Michinobu Tsuyoshi Journal of Materials Chemistry C 4 26 6200–6214 and in luminescence studies.Sukhikh Taisiya Ogienko D. Bashirov D. Konchenkoa S. May 21, 2019 Luminescent complexes of 2,1,3-benzothiadiazole derivatives Russian Chemical Bulletin 68 4 651–661 10.1007/s11172-019-2472-9 182415426 References Category:Benzothiadiazoles