Production Method 1

55919-82-9

885519-16-4

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: 4,5,6,7-Tetrachloro-2′,4′,5′,7′-tetraiodofluorescein Solvents: Acetonitrile ;  1 h, 20 °C

Reference

Bromination of indazoles enhanced by organic-dye, visible-light photoredox catalysis

Hornbrook, Lauren F.; Reed, Connor D.; Lamar, Angus A., Tetrahedron, 2023, 142,

3-Bromo-5-iodo-1H-indazole Raw materials

• 5-Iodo-1H-indazole

3-Bromo-5-iodo-1H-indazole Preparation Products

• 3-Bromo-5-iodo-1H-indazole (885519-16-4)

• 1. An approach to biodegradable star polymeric architectures using disulfide coupling?
  Jingquan Liu,Huiyun Liu,Zhongfan Jia,Volga Bulmus,Thomas P. Davis Chem. Commun., 2008, 6582-6584
• 2. Aggregation-induced emission enhancement of carbon quantum dots and applications in light emitting devices
  Rongyan Guo,Tao Li,Shuie Shi J. Mater. Chem. C, 2019,7, 5148-5154
• 3. An ATP-selective, lanthanide complex luminescent probe?
  Xiao Liu,Jun Xu,Yinyun Lv,Wenyu Wu,Weisheng Liu,Yu Tang Dalton Trans., 2013,42, 9840-9846
• 4. An integrated droplet-digital microfluidic system for on-demand droplet creation, mixing, incubation, and sorting?
  Lab Chip, 2019,19, 524-535
• 5. Aggregation dynamics, structure, and mechanical properties of bigels
  L. Di Michele,D. Fiocco,F. Varrato,E. Eiser,G. Foffi Soft Matter, 2014,10, 3633-3648

3-Bromo-5-iodo-1H-indazole: A Comprehensive Overview

3-Bromo-5-iodo-1H-indazole, also known by its CAS number 885519-16-4, is a heterocyclic organic compound with significant applications in various fields of chemistry and pharmacology. This compound belongs to the indazole family, which is a bicyclic structure consisting of a benzene ring fused to an imidazole ring. The presence of bromine and iodine substituents at the 3 and 5 positions, respectively, imparts unique electronic and structural properties to this molecule, making it a valuable compound in both academic research and industrial applications.

The synthesis of 3-Bromo-5-iodo-1H-indazole typically involves multi-step reactions, often starting from indole derivatives. Recent advancements in synthetic methodologies have enabled the efficient preparation of this compound with high purity and yield. Researchers have explored various strategies, including nucleophilic aromatic substitution, electrophilic substitution, and coupling reactions, to optimize the synthesis process. These methods not only enhance the scalability of production but also reduce the environmental footprint associated with traditional synthetic routes.

In terms of chemical properties, 3-Bromo-5-iodo-1H-indazole exhibits distinct reactivity due to the electron-withdrawing effects of bromine and iodine substituents. These substituents influence the electronic distribution within the indazole ring, making it more susceptible to various chemical transformations. For instance, the compound has been used as a precursor in the synthesis of bioactive molecules, where its reactivity plays a crucial role in forming complex structures with potential therapeutic applications.

The application of 3-Bromo-5-iodo-1H-indazole in drug discovery has garnered significant attention in recent years. Indazoles are known for their ability to modulate various biological targets, including kinases, ion channels, and receptors. The bromine and iodine substituents in this compound further enhance its bioactivity by introducing additional functional groups that can interact with biological systems. Studies have shown that derivatives of this compound exhibit promising anti-inflammatory, antitumor, and antimicrobial activities, making them strong candidates for further preclinical development.

Beyond pharmacology, 3-Bromo-5-iodo-1H-indazole has found applications in materials science. Its unique electronic properties make it a potential candidate for use in organic electronics, such as field-effect transistors (FETs) and light-emitting diodes (LEDs). Researchers have investigated its ability to form self-assembled monolayers (SAMs) on various substrates, which could be utilized in the development of advanced electronic devices with improved performance characteristics.

The structural versatility of 3-Bromo-5-iodo-1H-indazole also extends to its use as a building block in supramolecular chemistry. By exploiting non-covalent interactions such as hydrogen bonding and π–π stacking, this compound can be incorporated into supramolecular assemblies with tailored functionalities. Such assemblies have potential applications in sensing technologies, catalysis, and drug delivery systems.

In recent years, there has been growing interest in understanding the photophysical properties of 3-Bromo-5-Iodoindazoles. Studies have demonstrated that these compounds exhibit strong fluorescence emission under UV excitation due to their conjugated π-systems. This property makes them suitable for use as fluorescent probes in bioimaging applications. Researchers have explored their ability to detect metal ions and biomolecules with high sensitivity and selectivity.

The environmental impact of synthesizing and using CAS No 885519 - 16 - 4 compounds has also come under scrutiny. Efforts are being made to develop greener synthetic routes that minimize waste generation and reduce energy consumption. For instance, catalytic methods using transition metal catalysts or enzymes are being explored as alternatives to traditional high-energy reactions.

In conclusion, 3-Bromo - 5 - Iodo - 1 H - Indazole, identified by its CAS number CAS No 885519 - 16 - 4, is a versatile compound with diverse applications across multiple disciplines. Its unique chemical properties make it an invaluable tool for researchers working in drug discovery, materials science, supramolecular chemistry, and photophysics. As our understanding of this compound continues to grow through cutting-edge research initiatives worldwide,, its potential for innovative applications will undoubtedly expand further.

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