Cas no 885518-76-3 (3-Bromo-6-iodo-1H-indazole)

3-Bromo-6-iodo-1H-indazole is a halogenated indazole derivative commonly employed as a versatile intermediate in organic synthesis and pharmaceutical research. The presence of both bromo and iodo substituents at the 3- and 6-positions enhances its reactivity, facilitating selective cross-coupling reactions such as Suzuki, Sonogashira, and Buchwald-Hartwig transformations. This compound is particularly valuable in the development of heterocyclic compounds and biologically active molecules, including kinase inhibitors and other therapeutic agents. Its well-defined structure and high purity make it suitable for precise synthetic applications. The dual halogen functionality allows for sequential functionalization, offering flexibility in scaffold modification for medicinal chemistry and material science applications.
3-Bromo-6-iodo-1H-indazole structure
3-Bromo-6-iodo-1H-indazole structure
Product Name:3-Bromo-6-iodo-1H-indazole
CAS No:885518-76-3
MF:C7H4BrIN2
MW:322.928532600403
CID:840520
PubChem ID:24728225
Update Time:2025-06-30

3-Bromo-6-iodo-1H-indazole Chemical and Physical Properties

Names and Identifiers

    • 3-Bromo-6-iodo-1H-indazole
    • 3-Bromo-6-iodo (1H)indazole
    • 3-bromo-6-iodo-2H-indazole
    • G10395
    • FT-0727115
    • AKOS022172988
    • 885518-76-3
    • SCHEMBL18764465
    • DTXSID20646282
    • MB04927
    • 3-Bromo-6-iodo(1H)indazole
    • DB-077906
    • Inchi: 1S/C7H4BrIN2/c8-7-5-2-1-4(9)3-6(5)10-11-7/h1-3H,(H,10,11)
    • InChI Key: XILHFBUJIZYJRZ-UHFFFAOYSA-N
    • SMILES: IC1C=CC2=C(NN=C2C=1)Br

Computed Properties

  • Exact Mass: 321.86026g/mol
  • Monoisotopic Mass: 321.86026g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 155
  • 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: 3.2
  • Topological Polar Surface Area: 28.7?2

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Additional information on 3-Bromo-6-iodo-1H-indazole

Professional Introduction to 3-Bromo-6-iodo-1H-indazole (CAS No. 885518-76-3)

3-Bromo-6-iodo-1H-indazole is a highly versatile heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. With the CAS number 885518-76-3, this compound serves as a crucial intermediate in the synthesis of various biologically active molecules. Its unique structural features, comprising both bromo and iodo substituents on an indazole backbone, make it an attractive scaffold for further functionalization and derivatization.

The indazole core is a fused bicyclic structure consisting of a benzene ring and a pyrazole ring, which is known for its broad spectrum of biological activities. The presence of halogen atoms at the 3-position and 6-position enhances its reactivity, allowing for diverse chemical transformations. These properties have made 3-Bromo-6-iodo-1H-indazole a valuable building block in the development of novel therapeutic agents.

In recent years, there has been a surge in research focused on indazole derivatives due to their potential applications in treating various diseases, including cancer, infectious diseases, and neurological disorders. The halogenated indazoles, such as 3-Bromo-6-iodo-1H-indazole, have been particularly studied for their ability to interact with biological targets through halogen bonding and other non-covalent interactions.

One of the most compelling aspects of 3-Bromo-6-iodo-1H-indazole is its utility in cross-coupling reactions, which are fundamental to modern organic synthesis. The bromo and iodo substituents can be readily displaced by a wide range of nucleophiles via palladium-catalyzed reactions, such as Suzuki-Miyaura, Stille, and Buchwald-Hartwig couplings. These reactions enable the construction of complex molecular architectures, which are often essential for achieving high affinity and selectivity in drug design.

Recent studies have highlighted the use of 3-Bromo-6-iodo-1H-indazole in the synthesis of indazole-based inhibitors targeting protein-protein interactions. For instance, researchers have demonstrated its effectiveness in generating small molecules that disrupt critical cellular pathways involved in cancer progression. The ability to precisely modify the indazole scaffold allows for the optimization of pharmacokinetic properties and target engagement.

The pharmaceutical industry has also explored the potential of 3-Bromo-6-iodo-1H-indazole as a precursor for developing antiviral and antibacterial agents. By leveraging its reactivity, scientists have synthesized derivatives that exhibit inhibitory activity against various pathogens. This underscores the importance of halogenated indazoles in addressing emerging infectious diseases.

In addition to its role in drug discovery, 3-Bromo-6-iodo-1H-indazole has found applications in materials science. Its ability to form stable organometallic complexes has been exploited in the development of luminescent materials and catalysts. These applications demonstrate the broad utility of this compound beyond traditional pharmaceutical contexts.

The synthetic accessibility of 3-Bromo-6-iodo-1H-indazole is another key factor contributing to its widespread use. Several methods have been reported for its preparation, including halogenation reactions on pre-formed indazole derivatives. These synthetic routes are often scalable and compatible with industrial production standards, making 3-Bromo-6-iodo-1H-indazole a practical choice for both academic and industrial researchers.

The future prospects for 3-Bromo-6-iodo-1H-indazole are promising, with ongoing research aimed at expanding its chemical space and exploring new biological functions. Advances in computational chemistry and high-throughput screening techniques are expected to accelerate the discovery of novel derivatives with enhanced therapeutic potential.

In conclusion, 3-Bromo-6-iodo-1H-indazole (CAS No. 885518-76-3) is a multifaceted compound with significant implications in pharmaceutical chemistry and beyond. Its unique structural features, reactivity, and synthetic versatility make it an indispensable tool for researchers striving to develop innovative treatments for human diseases. As our understanding of its properties continues to grow, so too will its applications across various scientific disciplines.

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