Cas no 865156-34-9 (1H-INDAZOLE, 5-BROMO-3-IODO-1-METHYL-)

Technical Introduction: 1H-Indazole, 5-bromo-3-iodo-1-methyl-, is a halogenated indazole derivative featuring bromine and iodine substituents at the 5- and 3-positions, respectively, along with a methyl group at the 1-position. This compound serves as a versatile intermediate in organic synthesis, particularly in pharmaceutical and agrochemical research, due to its reactive halogen atoms that facilitate further functionalization. The presence of both bromo and iodo groups enhances its utility in cross-coupling reactions, such as Suzuki or Sonogashira couplings, enabling precise structural modifications. Its stable indazole core and defined substitution pattern make it valuable for developing biologically active molecules or materials with tailored properties. Suitable for controlled reactions under inert conditions.
1H-INDAZOLE, 5-BROMO-3-IODO-1-METHYL- structure
865156-34-9 structure
Product Name:1H-INDAZOLE, 5-BROMO-3-IODO-1-METHYL-
CAS No:865156-34-9
MF:C8H6BrIN2
MW:336.955112934113
MDL:MFCD12756578
CID:3221873
PubChem ID:23156226
Update Time:2025-10-28

1H-INDAZOLE, 5-BROMO-3-IODO-1-METHYL- Chemical and Physical Properties

Names and Identifiers

    • 1H-INDAZOLE, 5-BROMO-3-IODO-1-METHYL-
    • AS-62354
    • 865156-34-9
    • KDKLJZGIJMKMRP-UHFFFAOYSA-N
    • W19132
    • TQP1108
    • 5-bromo-3-iodo-1-methylindazole
    • EN300-7357646
    • DB-100210
    • AKOS037645694
    • CS-0456623
    • 5-bromo-3-iodo-1-methyl-1H-indazole
    • SCHEMBL1047954
    • MDL: MFCD12756578
    • Inchi: 1S/C8H6BrIN2/c1-12-7-3-2-5(9)4-6(7)8(10)11-12/h2-4H,1H3
    • InChI Key: KDKLJZGIJMKMRP-UHFFFAOYSA-N
    • SMILES: IC1C2C=C(C=CC=2N(C)N=1)Br

Computed Properties

  • Exact Mass: 335.87591g/mol
  • Monoisotopic Mass: 335.87591g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 0
  • Complexity: 178
  • 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: 2.9
  • Topological Polar Surface Area: 17.8?2

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Additional information on 1H-INDAZOLE, 5-BROMO-3-IODO-1-METHYL-

Professional Introduction to Compound with CAS No. 865156-34-9 and Product Name: 1H-INDAZOLE, 5-BROMO-3-IODO-1-METHYL

1H-INDAZOLE, 5-BROMO-3-IODO-1-METHYL (CAS No. 865156-34-9) is a highly specialized heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound belongs to the indazole family, which is known for its diverse biological activities and potential therapeutic applications. The structural features of this molecule, particularly the presence of bromo and iodo substituents at the 5th and 3rd positions respectively, make it a valuable intermediate in the synthesis of more complex pharmacophores.

The indazole core is a fused bicyclic structure consisting of a benzene ring and a pyrrole ring, which is a common motif in many biologically active natural products and synthetic drugs. The introduction of halogen atoms such as bromine and iodine at specific positions on the indazole ring enhances its reactivity, making it a versatile building block for further chemical modifications. These modifications can lead to the development of novel compounds with enhanced pharmacological properties.

In recent years, 1H-INDAZOLE, 5-BROMO-3-IODO-1-METHYL has been extensively studied for its potential in drug discovery. One of the most promising areas of research is its application in the development of anticancer agents. The halogenated indazoles have shown remarkable activity against various cancer cell lines by inhibiting key enzymes and pathways involved in tumor growth and progression. For instance, studies have demonstrated that compounds derived from this scaffold can selectively target cancer cells while minimizing toxicity to healthy cells.

Moreover, the bromo and iodo substituents on the indazole ring facilitate cross-coupling reactions, such as Suzuki-Miyaura and Sonogashira couplings, which are widely used in organic synthesis to construct complex molecular architectures. These reactions allow for the introduction of additional functional groups at various positions on the indazole core, enabling the creation of highly customized pharmacophores. Such flexibility is crucial for optimizing drug-like properties such as solubility, bioavailability, and metabolic stability.

Recent advancements in medicinal chemistry have highlighted the importance of 1H-INDAZOLE, 5-BROMO-3-IODO-1-METHYL in the development of next-generation therapeutics. For example, researchers have utilized this compound as a precursor in the synthesis of kinase inhibitors, which are essential for treating diseases such as leukemia and breast cancer. The ability to precisely modify the indazole scaffold allows for the fine-tuning of binding interactions with target proteins, leading to more effective and selective drug candidates.

The pharmaceutical industry has also shown interest in 1H-INDAZOLE, 5-BROMO-3-IODO-1-METHYL for its potential in addressing neurological disorders. Preliminary studies suggest that derivatives of this compound may exhibit neuroprotective effects by modulating neurotransmitter systems involved in conditions such as Alzheimer's disease and Parkinson's disease. The halogenated indazoles have demonstrated the ability to cross the blood-brain barrier, making them promising candidates for central nervous system (CNS) drug development.

In addition to its therapeutic applications, 1H-INDAZOLE, 5-BROMO-3-IODO-1-METHYL has found utility in materials science. The unique electronic properties of halogenated indazoles make them suitable for use in organic light-emitting diodes (OLEDs) and other optoelectronic devices. By tuning the substitution pattern on the indazole ring, researchers can modulate light emission characteristics, leading to advancements in display technologies and lighting solutions.

The synthesis of 1H-INDAZOLE, 5-BROMO-3-IODO-1-METHYL involves multi-step organic transformations that require careful optimization to ensure high yield and purity. Common synthetic routes include halogenation reactions followed by methylation at the 1-position of the indazole core. The use of palladium catalysts in cross-coupling reactions is often employed to achieve high selectivity and efficiency. Advances in green chemistry principles have also led to the development of more sustainable synthetic methods that minimize waste and reduce environmental impact.

The biological activity of 1H-INDAZOLE, 5-BROMO-3-IODO-1-METHYL is influenced by various factors including steric hindrance, electronic distribution, and solubility. Computational modeling techniques such as molecular docking and quantum mechanical calculations are increasingly used to predict binding affinities and optimize lead structures. These computational tools help researchers design molecules with improved pharmacokinetic properties and reduced side effects.

In conclusion,1H-INDAZOLE, 5-BROMO-3-IODO-1-METHYL (CAS No. 865156-34-9) is a multifaceted compound with significant potential in pharmaceutical research and industrial applications. Its unique structural features make it an invaluable intermediate for synthesizing novel therapeutics targeting various diseases. As research continues to uncover new biological activities and synthetic methodologies,1H-INDAZOLE, 5-BROMO, 3-IODO, and Methyl derivatives are likely to play an increasingly important role in shaping future medical treatments.

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