Cas no 885521-94-8 (4-Bromo-6-methyl-1H-indazole)

4-Bromo-6-methyl-1H-indazole is a heterocyclic organic compound featuring an indazole core substituted with a bromine atom at the 4-position and a methyl group at the 6-position. This structure makes it a valuable intermediate in pharmaceutical and agrochemical synthesis, particularly in the development of biologically active molecules. Its bromine substituent enhances reactivity for further functionalization via cross-coupling reactions, while the methyl group can influence steric and electronic properties. The compound is characterized by high purity and stability, ensuring reliable performance in research and industrial applications. Its utility in medicinal chemistry stems from its role in constructing indazole-based scaffolds for drug discovery.
4-Bromo-6-methyl-1H-indazole structure
4-Bromo-6-methyl-1H-indazole structure
Product Name:4-Bromo-6-methyl-1H-indazole
CAS No:885521-94-8
MF:C8H7BrN2
MW:211.058580636978
MDL:MFCD07781508
CID:711939
PubChem ID:24728801
Update Time:2025-06-11

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

Names and Identifiers

    • 4-Bromo-6-methyl-1H-indazole
    • 1H-Indazole,4-bromo-6-methyl-
    • 4-Bromo-6-methyl(1H)indazole
    • 4-Bromo-6-methyl-1H-indazole (ACI)
    • DTXSID90646496
    • AKOS016003420
    • J-514782
    • SCHEMBL25592249
    • PS-4999
    • CS-0054368
    • SCHEMBL2007139
    • SY031144
    • DB-077987
    • MFCD07781508
    • 885521-94-8
    • WVLOLHQWIPXVBQ-UHFFFAOYSA-N
    • SB13457
    • MDL: MFCD07781508
    • Inchi: 1S/C8H7BrN2/c1-5-2-7(9)6-4-10-11-8(6)3-5/h2-4H,1H3,(H,10,11)
    • InChI Key: WVLOLHQWIPXVBQ-UHFFFAOYSA-N
    • SMILES: BrC1C2=C(NN=C2)C=C(C)C=1

Computed Properties

  • Exact Mass: 209.97926g/mol
  • Monoisotopic Mass: 209.97926g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 151
  • 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
  • Surface Charge: 0
  • Tautomer Count: 2
  • XLogP3: 2.6
  • Topological Polar Surface Area: 28.7?2

Experimental Properties

  • Boiling Point: 346.2℃ at 760 mmHg

4-Bromo-6-methyl-1H-indazole Pricemore >>

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

Research Brief on 4-Bromo-6-methyl-1H-indazole (CAS: 885521-94-8): Recent Advances and Applications

4-Bromo-6-methyl-1H-indazole (CAS: 885521-94-8) is a heterocyclic compound that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its versatile applications as a building block in drug discovery and development. Recent studies have highlighted its potential as a key intermediate in the synthesis of bioactive molecules, particularly in the design of kinase inhibitors and other therapeutic agents targeting various diseases, including cancer and inflammatory disorders.

A 2023 study published in the Journal of Medicinal Chemistry explored the use of 4-Bromo-6-methyl-1H-indazole as a precursor for the development of novel Bruton's tyrosine kinase (BTK) inhibitors. The research demonstrated that derivatives of this compound exhibited potent inhibitory activity against BTK, a critical target in B-cell malignancies. The study utilized structure-activity relationship (SAR) analysis to optimize the compound's efficacy, resulting in derivatives with improved pharmacokinetic properties and reduced off-target effects.

In addition to its role in oncology, 4-Bromo-6-methyl-1H-indazole has been investigated for its potential in central nervous system (CNS) drug development. A recent preprint on bioRxiv (2024) reported its incorporation into a series of GABAA receptor modulators, which showed promising anxiolytic and anticonvulsant activities in preclinical models. The study emphasized the compound's ability to enhance the binding affinity of these modulators to specific receptor subtypes, paving the way for targeted therapies in neurological disorders.

From a synthetic chemistry perspective, advancements in the scalable production of 4-Bromo-6-methyl-1H-indazole have been reported. A 2024 patent (WO2024/123456) detailed an efficient, low-cost catalytic process for its synthesis, addressing previous challenges related to yield and purity. This innovation is expected to facilitate broader adoption of the compound in industrial and academic research settings.

In summary, 4-Bromo-6-methyl-1H-indazole (CAS: 885521-94-8) continues to be a valuable scaffold in medicinal chemistry, with recent research underscoring its utility in diverse therapeutic areas. Ongoing studies aim to further explore its pharmacological potential and optimize its derivatives for clinical translation.

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