Cas no 885518-97-8 (4-Bromo-6-iodo-1H-indazole)

4-Bromo-6-iodo-1H-indazole is a halogenated indazole derivative widely used as a versatile intermediate in pharmaceutical and agrochemical research. Its distinct bromo- and iodo-substitutions at the 4- and 6-positions enhance reactivity, enabling selective cross-coupling reactions such as Suzuki or Buchwald-Hartwig amination. The compound's rigid indazole core contributes to its stability, making it suitable for constructing complex heterocyclic frameworks. It is particularly valuable in medicinal chemistry for developing kinase inhibitors and other bioactive molecules. High purity and well-defined structural features ensure reproducibility in synthetic applications. Proper handling under inert conditions is recommended due to its sensitivity to light and moisture.
4-Bromo-6-iodo-1H-indazole structure
4-Bromo-6-iodo-1H-indazole structure
Product Name:4-Bromo-6-iodo-1H-indazole
CAS No:885518-97-8
MF:C7H4BrIN2
MW:322.928532600403
MDL:MFCD07781349
CID:840456
PubChem ID:24728097
Update Time:2025-06-10

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

Names and Identifiers

    • 4-Bromo-6-iodo-1H-indazole
    • 1H-Indazole,4-broMo-6-iodo-
    • AK102163
    • 4-broMo-6-iodo-1H indazole
    • BCP14798
    • FCH1324136
    • AX8233702
    • X6190
    • ST24043459
    • 4-Bromo-6-iodo-1H-indazole (ACI)
    • 1H-INDAZOLE, 4-BROMO-6-IODO-
    • AKOS016004233
    • SY112193
    • MFCD07781349
    • DS-3782
    • CS-0036583
    • F17481
    • SCHEMBL20176611
    • DTXSID80646162
    • 885518-97-8
    • DB-367573
    • PB43708
    • MDL: MFCD07781349
    • Inchi: 1S/C7H4BrIN2/c8-6-1-4(9)2-7-5(6)3-10-11-7/h1-3H,(H,10,11)
    • InChI Key: DHBZGMHXQRHPGP-UHFFFAOYSA-N
    • SMILES: BrC1C2=C(NN=C2)C=C(I)C=1

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: 1
  • 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
  • Topological Polar Surface Area: 28.7
  • XLogP3: 2.9

Experimental Properties

  • Density: 2.421±0.06 g/cm3 (20 oC 760 Torr),
  • Solubility: Very slightly soluble (0.12 g/l) (25 o C),

4-Bromo-6-iodo-1H-indazole Security Information

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Additional information on 4-Bromo-6-iodo-1H-indazole

Recent Advances in the Study of 4-Bromo-6-iodo-1H-indazole (CAS: 885518-97-8): A Comprehensive Research Brief

The compound 4-Bromo-6-iodo-1H-indazole (CAS: 885518-97-8) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its versatile applications in drug discovery and development. This heterocyclic scaffold is particularly valued for its role as a key intermediate in the synthesis of biologically active molecules, including kinase inhibitors and anticancer agents. Recent studies have explored its potential in modulating various signaling pathways, making it a promising candidate for therapeutic interventions.

One of the most notable advancements in the study of 4-Bromo-6-iodo-1H-indazole is its application in the development of targeted therapies for cancer. Researchers have demonstrated its efficacy in inhibiting specific protein kinases involved in tumor proliferation and metastasis. For instance, a 2023 study published in the Journal of Medicinal Chemistry highlighted its role as a precursor in the synthesis of potent inhibitors targeting the PI3K/AKT/mTOR pathway, which is frequently dysregulated in various cancers. The study reported significant reductions in tumor growth in preclinical models, underscoring the compound's therapeutic potential.

In addition to its anticancer properties, 4-Bromo-6-iodo-1H-indazole has also been investigated for its utility in medicinal chemistry as a building block for the design of novel bioactive compounds. Its unique structural features, including the presence of both bromo and iodo substituents, allow for diverse functionalization, enabling the creation of libraries of derivatives with varied pharmacological activities. Recent work published in Bioorganic & Medicinal Chemistry Letters detailed the synthesis and evaluation of such derivatives, revealing promising activity against infectious diseases and inflammatory conditions.

Another area of interest is the compound's role in chemical biology as a probe for studying enzyme mechanisms. The halogenated indazole core of 4-Bromo-6-iodo-1H-indazole makes it an excellent candidate for photoaffinity labeling and cross-linking studies, which are essential for elucidating protein-ligand interactions. A 2024 study in ACS Chemical Biology utilized this compound to investigate the binding dynamics of a novel class of enzymes involved in DNA repair, providing insights that could inform the design of next-generation therapeutics.

Despite these promising developments, challenges remain in optimizing the pharmacokinetic and pharmacodynamic properties of 4-Bromo-6-iodo-1H-indazole-derived compounds. Issues such as solubility, bioavailability, and off-target effects need to be addressed to facilitate their transition from bench to bedside. Ongoing research is focused on structural modifications and formulation strategies to overcome these hurdles, as evidenced by recent patents and preclinical studies.

In conclusion, 4-Bromo-6-iodo-1H-indazole (CAS: 885518-97-8) represents a valuable scaffold in chemical biology and pharmaceutical research, with applications ranging from anticancer drug development to enzyme mechanism studies. The latest research underscores its potential as a versatile tool for drug discovery, while also highlighting the need for further optimization to fully realize its therapeutic benefits. Continued exploration of this compound and its derivatives is expected to yield significant advancements in the treatment of various diseases.

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