Cas no 1159511-80-4 (5-bromo-1,4-dimethyl-indazole)

5-Bromo-1,4-dimethyl-indazole is a halogenated indazole derivative characterized by its bromine substitution at the 5-position and methyl groups at the 1- and 4-positions. This compound serves as a versatile intermediate in organic synthesis, particularly in the development of pharmacologically active molecules and heterocyclic compounds. The bromine atom enhances reactivity for further functionalization via cross-coupling reactions, while the methyl groups contribute to steric and electronic modulation. Its stable crystalline form and well-defined structure make it suitable for precise synthetic applications. The compound is commonly utilized in medicinal chemistry research for scaffold diversification and as a building block in the synthesis of potential bioactive agents.
5-bromo-1,4-dimethyl-indazole structure
5-bromo-1,4-dimethyl-indazole structure
Product Name:5-bromo-1,4-dimethyl-indazole
CAS No:1159511-80-4
MF:C9H9BrN2
MW:225.085160970688
MDL:MFCD12028624
CID:1040428
PubChem ID:44119457
Update Time:2025-06-09

5-bromo-1,4-dimethyl-indazole Chemical and Physical Properties

Names and Identifiers

    • 5-Bromo-1,4-dimethyl-1H-indazole
    • AG-C-05956
    • ANW-66201
    • CTK5I8265
    • MolPort-016-581-647
    • OR40128
    • 5-bromo-1,4-dimethyl-indazole
    • CS-0101154
    • SCHEMBL15518859
    • 1H-Indazole, 5-bromo-1,4-dimethyl-
    • J-516783
    • PS-5003
    • DA-19300
    • 1159511-80-4
    • DTXSID10657246
    • MFCD12028624
    • AKOS015950401
    • 5-bromo-1,4-dimethylindazole
    • DTXCID40607996
    • MDL: MFCD12028624
    • Inchi: 1S/C9H9BrN2/c1-6-7-5-11-12(2)9(7)4-3-8(6)10/h3-5H,1-2H3
    • InChI Key: WUBOGWOQGQGGGP-UHFFFAOYSA-N
    • SMILES: BrC1C=CC2=C(C=NN2C)C=1C

Computed Properties

  • Exact Mass: 223.99491g/mol
  • Monoisotopic Mass: 223.99491g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 0
  • Complexity: 174
  • 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: 2.6
  • Topological Polar Surface Area: 17.8?2

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Additional information on 5-bromo-1,4-dimethyl-indazole

Professional Introduction to Compound with CAS No. 1159511-80-4 and Product Name: 5-bromo-1,4-dimethyl-indazole

5-bromo-1,4-dimethyl-indazole, identified by the Chemical Abstracts Service (CAS) number 1159511-80-4, is a heterocyclic organic compound that has garnered significant attention in the field of pharmaceutical and medicinal chemistry. This compound belongs to the indazole class, characterized by a benzene ring fused to a pyrrole ring, with substituents that modify its chemical and biological properties. The presence of a bromine atom at the 5-position and methyl groups at the 1 and 4 positions introduces unique reactivity and potential pharmacological activity, making it a valuable scaffold for drug discovery and development.

The structural features of 5-bromo-1,4-dimethyl-indazole make it a versatile intermediate in organic synthesis. The bromine substituent, in particular, serves as a reactive handle for further functionalization through cross-coupling reactions such as Suzuki-Miyaura, Heck, and Buchwald-Hartwig couplings. These reactions are widely employed in the construction of complex molecular architectures, enabling the synthesis of novel compounds with tailored biological activities. The methyl groups at the 1 and 4 positions contribute to the compound's stability and influence its electronic properties, affecting both its reactivity and interactions with biological targets.

In recent years, indazole derivatives have been extensively studied for their potential therapeutic applications. The indazole core is found in several bioactive molecules, including antimicrobial, antiviral, anti-inflammatory, and anticancer agents. The brominated and dimethyl-substituted indazoles have shown promise in preclinical studies as scaffolds for developing small-molecule inhibitors targeting various disease pathways. For instance, derivatives of 5-bromo-1,4-dimethyl-indazole have been investigated for their ability to modulate enzyme activity and interfere with protein-protein interactions relevant to cancer progression.

One of the most compelling aspects of 5-bromo-1,4-dimethyl-indazole is its role in the development of kinase inhibitors. Kinases are enzymes that play crucial roles in cell signaling pathways, and their dysregulation is often associated with diseases such as cancer. By designing molecules that selectively inhibit specific kinases, researchers aim to develop treatments that disrupt aberrant signaling networks without harming healthy cells. The bromine atom in 5-bromo-1,4-dimethyl-indazole allows for modifications that can enhance binding affinity to kinase active sites, while the methyl groups help optimize steric interactions with the target protein.

Recent advancements in computational chemistry have further enhanced the utility of 5-bromo-1,4-dimethyl-indazole as a drug discovery tool. Molecular modeling techniques predict how different substituents affect the compound's binding affinity and selectivity for biological targets. These predictions guide synthetic efforts toward optimizing lead compounds for clinical trials. Additionally, high-throughput screening (HTS) methods have been employed to rapidly test large libraries of indazole derivatives for activity against disease-relevant targets. Such approaches have led to the identification of several promising candidates derived from 5-bromo-1,4-dimethyl-indazole that are now undergoing further investigation.

The pharmacokinetic properties of 5-bromo-1,4-dimethyl-indazole are also an area of active research. Understanding how a compound is absorbed, distributed, metabolized, and excreted (ADME) is critical for determining its potential as a drug candidate. Studies have shown that modifications around the indazole core can significantly impact these properties. For example, optimizing solubility and metabolic stability can improve bioavailability and reduce toxicity. Researchers are exploring various strategies to fine-tune these parameters while maintaining or enhancing biological activity.

In conclusion,5-bromo-1,4-dimethyl-indazole (CAS No. 1159511-80-4) represents a significant advancement in medicinal chemistry due to its structural versatility and potential therapeutic applications. Its role as a building block for kinase inhibitors and other bioactive molecules underscores its importance in drug discovery efforts aimed at treating diseases such as cancer. As research continues to uncover new ways to leverage this compound's unique properties,5-bromo-1,4-dimethyl-indazole is poised to remain at the forefront of pharmaceutical innovation.

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