Cas no 929617-32-3 (4-Bromo-3-chloro-6-nitro-1h-indazole)

4-Bromo-3-chloro-6-nitro-1H-indazole is a heterocyclic compound featuring a bromo, chloro, and nitro substituent on an indazole core. This multifunctional scaffold is valuable in medicinal chemistry and pharmaceutical research, serving as a versatile intermediate for the synthesis of biologically active molecules. Its electron-withdrawing groups enhance reactivity, making it suitable for cross-coupling reactions and further functionalization. The compound's structural features contribute to its utility in developing kinase inhibitors and other therapeutic agents. High purity and well-defined reactivity ensure consistent performance in synthetic applications. Proper handling and storage are recommended due to its sensitivity to light and moisture.
4-Bromo-3-chloro-6-nitro-1h-indazole structure
929617-32-3 structure
Product Name:4-Bromo-3-chloro-6-nitro-1h-indazole
CAS No:929617-32-3
MF:C7H3BrClN3O2
MW:276.474619150162
MDL:MFCD13177079
CID:1033487
PubChem ID:70680679
Update Time:2025-05-21

4-Bromo-3-chloro-6-nitro-1h-indazole Chemical and Physical Properties

Names and Identifiers

    • 5-Bromo-3-chloro-6-nitro-1H-indazole
    • 5-bromo-3-chloro-6-nitro-2H-indazole
    • CS-0367167
    • SCHEMBL16213299
    • LFBVQNHVYIPVOU-UHFFFAOYSA-N
    • AKOS016844991
    • DTXSID20742632
    • 929617-32-3
    • AM20120452
    • 1H-Indazole, 5-bromo-3-chloro-6-nitro-
    • DB-317456
    • 4-Bromo-3-chloro-6-nitro-1h-indazole
    • MDL: MFCD13177079
    • Inchi: 1S/C7H3BrClN3O2/c8-4-1-3-5(10-11-7(3)9)2-6(4)12(13)14/h1-2H,(H,10,11)
    • InChI Key: LFBVQNHVYIPVOU-UHFFFAOYSA-N
    • SMILES: BrC1C(=CC2C(=C(NN=2)Cl)C=1)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 274.90972g/mol
  • Monoisotopic Mass: 274.90972g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 1
  • Complexity: 250
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 3
  • Topological Polar Surface Area: 74.5?2

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Additional information on 4-Bromo-3-chloro-6-nitro-1h-indazole

4-Bromo-3-chloro-6-nitro-1H-indazole (CAS No. 929617-32-3): A Comprehensive Overview

4-Bromo-3-chloro-6-nitro-1H-indazole (CAS No. 929617-32-3) is a highly functionalized heterocyclic compound belonging to the indazole family. This compound has garnered significant attention in the fields of organic chemistry, pharmacology, and materials science due to its unique structural features and versatile reactivity. The molecule consists of an indazole core, which is a bicyclic structure comprising a benzene ring fused with a pyrazole ring. The substitution pattern of this compound includes a bromine atom at position 4, a chlorine atom at position 3, and a nitro group at position 6, making it a valuable substrate for various chemical transformations and applications.

The synthesis of 4-bromo-3-chloro-6-nitroindazole involves multi-step processes that typically begin with the preparation of the indazole scaffold. Recent advancements in synthetic methodologies have enabled the efficient construction of such complex molecules with high purity and yield. For instance, researchers have explored the use of transition metal catalysts to facilitate key steps such as bromination and nitration, ensuring precise control over the substitution pattern. These studies highlight the importance of understanding reaction mechanisms and optimizing synthetic pathways to achieve desired products.

One of the most intriguing aspects of 4-bromoindazole derivatives is their potential in drug discovery. The presence of electron-withdrawing groups like bromine, chlorine, and nitro groups enhances the molecule's ability to interact with biological targets, making it a promising candidate for designing bioactive compounds. Recent studies have demonstrated that 4-bromoindazoles can exhibit potent inhibitory activity against various enzymes implicated in diseases such as cancer and neurodegenerative disorders. For example, researchers have reported that certain derivatives can modulate kinase activity, suggesting their potential as therapeutic agents.

In addition to its pharmacological applications, 4-bromoindazole has also found utility in materials science. The molecule's aromaticity and conjugation make it suitable for applications in organic electronics. Recent research has focused on incorporating 4-bromoindazoles into π-conjugated systems to enhance charge transport properties in organic semiconductors. These studies underscore the compound's versatility and its role in advancing next-generation electronic materials.

The chemical reactivity of 4-bromoindazole is another area that has been extensively studied. The presence of multiple electron-withdrawing groups renders the molecule highly reactive under certain conditions. For instance, bromination at position 4 facilitates further functionalization through nucleophilic aromatic substitution reactions. Similarly, the nitro group at position 6 can be reduced to an amino group, enabling access to a wide range of derivatives with diverse functionalities.

From an environmental standpoint, understanding the fate and behavior of 4-bromoindazoles in natural systems is crucial for assessing their potential impact on ecosystems. Recent studies have investigated the degradation pathways of such compounds under various environmental conditions, providing insights into their persistence and toxicity. These findings are essential for guiding safe handling practices and minimizing ecological risks associated with their use.

In conclusion, 4-bromoindazole (CAS No. 929617-32-3) stands out as a multifaceted compound with significant implications across multiple scientific disciplines. Its unique structure, reactivity, and functionalization potential continue to drive innovative research efforts aimed at unlocking its full potential in drug discovery, materials science, and beyond.

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