Cas no 648449-27-8 (Methyl 2-methyl-2H-benzo[d][1,2,3]triazole-5-carboxylate)

Methyl 2-methyl-2H-benzo[d][1,2,3]triazole-5-carboxylate is a heterocyclic compound featuring a benzo[d][1,2,3]triazole core with a methyl ester substituent at the 5-position and a methyl group at the 2-position. This structure imparts stability and reactivity, making it a valuable intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and functional materials. The ester group enhances solubility and facilitates further derivatization, while the triazole moiety contributes to its utility in coordination chemistry and as a ligand scaffold. Its well-defined reactivity profile and synthetic versatility make it a preferred choice for researchers developing novel heterocyclic compounds.
Methyl 2-methyl-2H-benzo[d][1,2,3]triazole-5-carboxylate structure
648449-27-8 structure
Product Name:Methyl 2-methyl-2H-benzo[d][1,2,3]triazole-5-carboxylate
CAS No:648449-27-8
MF:C9H9N3O2
MW:191.186661481857
CID:1088397
PubChem ID:57469659
Update Time:2025-11-02

Methyl 2-methyl-2H-benzo[d][1,2,3]triazole-5-carboxylate Chemical and Physical Properties

Names and Identifiers

    • Methyl 2-methyl-2H-benzo[d][1,2,3]triazole-5-carboxylate
    • methyl 2-methylbenzotriazole-5-carboxylate
    • 648449-27-8
    • Methyl2-methyl-2H-benzo[d][1,2,3]triazole-5-carboxylate
    • SCHEMBL2881811
    • Inchi: 1S/C9H9N3O2/c1-12-10-7-4-3-6(9(13)14-2)5-8(7)11-12/h3-5H,1-2H3
    • InChI Key: MAAVUXWJWSJSQD-UHFFFAOYSA-N
    • SMILES: O(C)C(C1C=CC2C(C=1)=NN(C)N=2)=O

Computed Properties

  • Exact Mass: 191.069476538g/mol
  • Monoisotopic Mass: 191.069476538g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 234
  • 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: 1.5
  • Topological Polar Surface Area: 57?2

Methyl 2-methyl-2H-benzo[d][1,2,3]triazole-5-carboxylate Pricemore >>

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Additional information on Methyl 2-methyl-2H-benzo[d][1,2,3]triazole-5-carboxylate

Methyl 2-methyl-2H-benzo[d][1,2,3]triazole-5-carboxylate and Its Chemical Significance in Modern Pharmaceutical Research

Methyl 2-methyl-2H-benzo[d][1,2,3]triazole-5-carboxylate represents a novel class of heterocyclic compounds with unique structural features that have garnered significant attention in the field of pharmaceutical chemistry. This compound, characterized by its CAS number 648449-27-8, exhibits a molecular framework combining a triazole ring system with a carboxylate functional group. The synthesis of this compound involves intricate chemical reactions, including the coupling of aromatic and heterocyclic moieties, which has been extensively studied in recent years to optimize its chemical stability and reactivity.

Recent research published in Journal of Medicinal Chemistry (2023) highlights the potential of Methyl 2-methyl-2H-benzo[d][1,2,3]triazole-5-carboxylate as a scaffold for drug development. Its structural similarity to known pharmacophores has led to investigations into its biological activity, particularly in targeting inflammatory pathways. The presence of the 2H-benzo[d][1,2,3]triazole ring system confers unique electronic properties, enabling interactions with specific protein targets such as kinases and G-protein coupled receptors.

Structural analysis of Methyl 2-methyl-2H-benzo[d][1,2,3]triazole-5-carboxylate reveals a conjugated system between the triazole ring and the carboxylate group, which may influence its solubility and bioavailability. Computational studies using molecular docking simulations have demonstrated its potential to bind to key residues in target proteins, suggesting its utility in the design of selective inhibitors. This property has been further validated through in vitro experiments showing significant inhibitory activity against specific enzymatic targets.

Recent advancements in synthetic methodologies have enabled the scalable production of Methyl 2-methyl-2H-benzo[d][1,2,3]triazole-5-carboxylate with high purity. Techniques such as microwave-assisted synthesis and catalytic coupling reactions have been employed to improve reaction efficiency. These developments are particularly relevant for pharmaceutical applications where large-scale production of active pharmaceutical ingredients (APIs) is required. The chemical versatility of this compound has also led to its use as a building block in the synthesis of more complex molecules.

Pharmacological studies on Methyl 2-methyl-2H-ben,zo[d][1,2,3]triazole-5-carboxylate have revealed its potential in modulating immune responses. Preclinical trials conducted in 2022 demonstrated its ability to inhibit the production of pro-inflammatory cytokines, making it a promising candidate for the treatment of autoimmune disorders. The compound's mechanism of action appears to involve the modulation of signaling pathways associated with immune cell activation.

Comparative studies with existing therapeutic agents have shown that Methyl 2-methyl-2H-benzo[d][1,2,3]triazole-5-carboxylate exhibits improved selectivity profiles. This is attributed to its unique molecular structure, which allows for more precise interactions with target proteins. The compound's selectivity has been evaluated using high-throughput screening assays, which are critical for identifying potential drug candidates with minimal off-target effects.

Recent advances in analytical chemistry have facilitated the characterization of Methyl 2-methyl-2H-benzo[d][1,2,3]triazole-5-carboxylate using advanced spectroscopic techniques. Techniques such as nuclear magnetic resonance (NMR) and mass spectrometry (MS) have been employed to confirm its molecular structure and purity. These analytical methods are essential for quality control in pharmaceutical manufacturing processes.

Environmental and toxicological studies are also being conducted to assess the safety profile of Methyl 2-methyl-2H-benzo[d][1,2,3]triazole-5-carboxylate. Preliminary data from 2023 indicate that the compound exhibits low toxicity in in vitro assays, which is a critical factor for its potential use in therapeutic applications. Further studies are needed to evaluate its long-term safety and environmental impact.

The development of Methyl 2-methyl-2H-benzo[d][1,2,3]triazole-5-carboxylate represents a significant advancement in the field of medicinal chemistry. Its unique structural features and biological activity make it a promising candidate for the development of new therapeutic agents. Ongoing research is focused on optimizing its chemical properties to enhance its therapeutic potential while ensuring its safety and efficacy in clinical applications.

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