Cas no 1234615-89-4 (2,3-dimethylindazole-6-carbonitrile)

2,3-Dimethylindazole-6-carbonitrile is a heterocyclic organic compound featuring an indazole core substituted with methyl groups at the 2- and 3-positions and a cyano group at the 6-position. This structure imparts versatility in pharmaceutical and agrochemical applications, serving as a key intermediate in the synthesis of biologically active molecules. The electron-withdrawing nitrile group enhances reactivity, facilitating further functionalization, while the methyl substitutions contribute to steric and electronic modulation. Its well-defined crystalline form ensures high purity and stability, making it suitable for precision chemical synthesis. The compound is particularly valuable in medicinal chemistry for developing targeted inhibitors and ligands due to its balanced lipophilicity and structural rigidity.
2,3-dimethylindazole-6-carbonitrile structure
1234615-89-4 structure
Product Name:2,3-dimethylindazole-6-carbonitrile
CAS No:1234615-89-4
MF:C10H9N3
MW:171.198561429977
CID:2618482
PubChem ID:72207497
Update Time:2025-11-02

2,3-dimethylindazole-6-carbonitrile Chemical and Physical Properties

Names and Identifiers

    • 2,3-dimethylindazole-6-carbonitrile
    • DTXSID101280375
    • CS-0055218
    • P12037
    • 1234615-89-4
    • 6-CYANO-2,3-DIMETHYL-2H-INDAZOLE
    • 2,3-Dimethyl-2H-indazole-6-carbonitrile
    • PB27077
    • Inchi: 1S/C10H9N3/c1-7-9-4-3-8(6-11)5-10(9)12-13(7)2/h3-5H,1-2H3
    • InChI Key: XTTAVCHNDBUURN-UHFFFAOYSA-N
    • SMILES: N1(C)C(C)=C2C=CC(C#N)=CC2=N1

Computed Properties

  • Exact Mass: 171.079647300Da
  • Monoisotopic Mass: 171.079647300Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 0
  • Complexity: 242
  • 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: 1.7
  • Topological Polar Surface Area: 41.6?2

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Additional information on 2,3-dimethylindazole-6-carbonitrile

Exploring the Versatile Applications of 2,3-Dimethylindazole-6-Carbonitrile (CAS No. 1234615-89-4) in Modern Chemistry

2,3-Dimethylindazole-6-carbonitrile (CAS No. 1234615-89-4) is a specialized heterocyclic compound that has garnered significant attention in pharmaceutical and material science research. This nitrogen-containing heterocycle features a unique molecular structure combining an indazole core with methyl substituents and a cyano group, making it valuable for various synthetic applications. Researchers particularly value its role as a versatile building block in medicinal chemistry, where it serves as a precursor for numerous biologically active molecules.

The growing interest in indazole derivatives like 2,3-dimethylindazole-6-carbonitrile stems from their remarkable pharmacological potential. Current trends in drug discovery emphasize the development of small molecule inhibitors targeting protein kinases, and this compound's structural features make it an excellent candidate for such applications. Its electron-withdrawing cyano group and methyl substitutions contribute to enhanced metabolic stability and improved binding affinity – two critical factors in modern drug design.

Beyond pharmaceutical applications, 2,3-dimethylindazole-6-carbonitrile shows promise in materials science. Its molecular architecture suggests potential utility in developing organic electronic materials, particularly as a component in OLED (organic light-emitting diode) technologies. The compound's conjugated system and electron-deficient character make it interesting for researchers exploring novel charge transport materials for next-generation displays and lighting solutions.

Synthetic chemists appreciate 2,3-dimethylindazole-6-carbonitrile for its relatively straightforward preparation from commercially available starting materials. The standard synthetic route typically involves cyclization reactions of appropriately substituted precursors, followed by cyanation reactions to introduce the nitrile functionality. Recent advances in catalytic cyanation methods have improved the efficiency of producing such compounds, addressing growing industrial demand.

The physicochemical properties of 2,3-dimethylindazole-6-carbonitrile contribute to its widespread utility. With moderate solubility in common organic solvents and good thermal stability, this compound handles well in various reaction conditions. Its molecular weight of 185.22 g/mol and balanced lipophilicity profile make it particularly suitable for medicinal chemistry applications where such parameters critically influence drug-like properties.

Recent patent literature reveals increasing interest in 2,3-dimethylindazole-6-carbonitrile derivatives as potential therapeutics for neurological disorders. Several research groups have reported promising activity of related compounds as modulators of neurotransmitter systems, particularly in targeting receptors implicated in anxiety and depression. This aligns with current pharmaceutical industry focus on central nervous system (CNS) drugs to address growing mental health concerns worldwide.

Quality control of 2,3-dimethylindazole-6-carbonitrile typically involves analytical techniques such as HPLC (High Performance Liquid Chromatography) and NMR spectroscopy. These methods ensure the compound meets the stringent purity requirements for research and development applications. The availability of high-purity material (typically >98%) from specialty chemical suppliers facilitates its adoption across various research programs.

Environmental and safety considerations for 2,3-dimethylindazole-6-carbonitrile follow standard laboratory chemical handling protocols. While not classified as hazardous under current regulations, proper personal protective equipment (PPE) including gloves and safety glasses is recommended when handling this compound. Storage under inert atmosphere at controlled temperatures helps maintain its stability over extended periods.

The commercial availability of 2,3-dimethylindazole-6-carbonitrile from multiple global suppliers reflects its growing importance in chemical research. Current market trends show steady demand from both academic institutions and pharmaceutical companies, with projected growth as more applications emerge in drug discovery pipelines and material science innovations.

Future research directions for 2,3-dimethylindazole-6-carbonitrile likely include exploration of its photophysical properties for optoelectronic applications and further investigation of its pharmacological potential. The compound's versatility ensures it will remain a valuable tool for chemists working across multiple disciplines, from medicinal chemistry to advanced materials development.

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