• 1. Emerging enantiomeric resolution materials with homochiral nano-fabrications
  Ji-Ping Wei Nanoscale, 2015,7, 11815-11832
• 2. Disulfide- and terminal alkyne-functionalized magnetic silica particles for enrichment of azido glycopeptides?
  Sheng Wang,Wenxian Xie,Xiu Zhang,Xia Zou,Yan Zhang Chem. Commun., 2012,48, 5907-5909
• 3. Examination of ammonia–poly(pyrrole) interactions by piezoelectric and conductivity measurements
  Analyst, 1991,116, 1125-1130
• 4. Excimer emission and magnetoluminescence of radical-based zinc(ii) complexes doped in host crystals?
  Shojiro Kimura,Tetsuro Kusamoto Chem. Commun., 2020,56, 11195-11198
• 5. Exciting clusters, what does off-resonance actually mean??
  Goonay Yousefalizadeh,Shideh Ahmadi,Nicholas J. Mosey,Kevin G. Stamplecoskie Nanoscale, 2021,13, 242-252

6-Bromo-4-methyl-2,1,3-benzothiadiazole (CAS No. 2411221-59-3): An Overview of Its Structure, Properties, and Applications in Modern Chemistry

6-Bromo-4-methyl-2,1,3-benzothiadiazole (CAS No. 2411221-59-3) is a versatile organic compound that has garnered significant attention in recent years due to its unique chemical structure and potential applications in various fields of chemistry and materials science. This compound belongs to the class of benzothiadiazoles, which are known for their electronic and optical properties. In this article, we will delve into the structure, synthesis, properties, and potential applications of 6-Bromo-4-methyl-2,1,3-benzothiadiazole.

Chemical Structure and Synthesis

The molecular formula of 6-Bromo-4-methyl-2,1,3-benzothiadiazole is C₈H₅BrN₂S. The compound features a benzene ring fused with a thiadiazole ring, with a bromine atom at the 6-position and a methyl group at the 4-position. The presence of these functional groups imparts unique chemical and physical properties to the molecule.

The synthesis of 6-Bromo-4-methyl-2,1,3-benzothiadiazole can be achieved through several methods. One common approach involves the reaction of 4-methylbenzothiadiazole with bromine or a brominating agent such as N-bromosuccinimide (NBS). This reaction typically proceeds via electrophilic aromatic substitution, leading to the formation of the desired product. The reaction conditions, such as temperature and solvent choice, can significantly influence the yield and purity of the final product.

Physical and Chemical Properties

6-Bromo-4-methyl-2,1,3-benzothiadiazole is a solid compound with a melting point typically ranging from 150°C to 155°C. It is insoluble in water but exhibits good solubility in organic solvents such as dimethylformamide (DMF), dimethyl sulfoxide (DMSO), and dichloromethane (DCM). The compound's solubility characteristics make it suitable for various synthetic transformations and material applications.

The electronic structure of 6-Bromo-4-methyl-2,1,3-benzothiadiazole is characterized by its conjugated π-electron system. The presence of the bromine atom introduces electron-withdrawing effects, which can influence the compound's electronic properties. These properties make it an attractive candidate for use in organic electronics and photovoltaic materials.

Spectroscopic Properties

The spectroscopic properties of 6-Bromo-4-methyl-2,1,3-benzothiadiazole have been extensively studied using techniques such as UV-visible spectroscopy and nuclear magnetic resonance (NMR) spectroscopy. UV-visible spectroscopy reveals strong absorption bands in the visible region due to π→π* transitions within the conjugated system. NMR spectroscopy provides detailed information about the molecular structure and dynamics.

In particular, the ¹H NMR spectrum of 6-Bromo-4-methyl-2,1,3-benzothiadiazole shows characteristic signals for the aromatic protons and the methyl group. The presence of these signals helps confirm the identity and purity of the compound. Additionally, mass spectrometry (MS) can be used to determine the molecular weight and confirm the presence of specific functional groups.

Potential Applications

The unique properties of 6-Bromo-4-methyl-2,1,3-benzothiadiazole have led to its exploration in various applications. One promising area is in organic electronics, where it can be used as a building block for organic semiconductors. The compound's ability to form stable thin films makes it suitable for use in organic field-effect transistors (OFETs) and organic photovoltaic cells (OPVs).

In addition to its use in electronics, 6-Bromo-4-methyl-2,1,3-benzothiadiazole has potential applications in materials science. Its high thermal stability and good mechanical properties make it an attractive candidate for use in polymer composites and coatings. Recent studies have also explored its use as a precursor for metalorganic frameworks (MOFs) due to its ability to form stable coordination bonds with metal ions.

Biochemical Applications

Beyond its use in materials science and electronics, 6-Bromo-4-methyl-2,1,3-benzothiadiazole has shown promise in biochemical research. The compound's ability to interact with biological systems has been investigated for potential therapeutic applications. For example, studies have explored its use as a scaffold for developing small molecule inhibitors targeting specific enzymes or receptors.

In one recent study published in the Journal of Medicinal Chemistry, researchers synthesized a series of derivatives based on 6-Bromo-4-methyl-2,1,3-benzothiadiazole. These derivatives were tested for their ability to inhibit kinases involved in cancer signaling pathways. The results showed that several compounds exhibited potent inhibitory activity against specific kinases without significant cytotoxicity towards normal cells.

Safety Considerations

< strong >Conclusion< / strong > p > < p >In summary,< strong >6-Bromo-4-methyl-2 , 1 , 3 - benzothiadiazole< / strong >( CAS No . 2411221 - 59 - 3 ) is a multifaceted compound with a rich array of potential applications . Its unique chemical structure , combined with its favorable physical properties , makes it an attractive candidate for use in various fields including organic electronics , materials science , and biochemical research . As research continues to advance , it is likely that new applications for this compound will emerge , further highlighting its importance in modern chemistry . p > article > < / response >

• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)
• 1449132-38-0(3-Fluoro-5-(2-fluoro-5-methylbenzylcarbamoyl)benzeneboronic acid)
• 2034271-14-0(2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide)