Cas no 4343-73-1 (ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate)

Ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate is a versatile heterocyclic compound featuring a triazole core with a methyl substituent at the 5-position and an ester functional group at the 4-position. This structure imparts reactivity suitable for further derivatization, making it valuable in pharmaceutical and agrochemical synthesis. The ester moiety allows for facile hydrolysis or transesterification, while the triazole ring offers stability and potential for diverse interactions. Its well-defined molecular framework ensures consistency in synthetic applications. The compound is typically supplied with high purity, ensuring reliable performance in research and industrial processes. Proper handling and storage under inert conditions are recommended to maintain stability.
ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate structure
4343-73-1 structure
Product Name:ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate
CAS No:4343-73-1
MF:C6H9N3O2
MW:155.154560804367
CID:330639
PubChem ID:78046
Update Time:2025-05-24

ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate Chemical and Physical Properties

Names and Identifiers

    • 1H-1,2,3-Triazole-5-carboxylicacid, 4-methyl-, ethyl ester
    • ETHYL 5-METHYL-1H-1,2,3-TRIAZOLE-4-CARBOXYLATE
    • 1H-1,2,3-Triazole-4-carboxylic acid, 5-methyl-, ethyl ester
    • ethyl 5-methyl-2H-1,2,3-triazole-4-carboxylate
    • 2,3-triazole-4-carboxylic acid, 5-methyl-1h- ethyl ester
    • 2,3-triazole-4-carboxylic acid, 5-methyl-1h- ethylester
    • 1H-1,2,3-Triazole-5-carboxylic acid, 4-methyl-, ethyl ester
    • Ethyl 4-methyl-1H-1,2,3-triazole-5-carboxylate
    • ethyl 5-methyl-2H-triazole-4-carboxylate
    • EN300-173461
    • BDBM50390970
    • 4343-73-1
    • 5-methyl-2H-[1,2,3]triazole-4-carboxylic acid ethyl ester
    • SCHEMBL841773
    • 5-methyl-2H-[1,2,3]-triazole-4-carboxylic acid ethyl ester
    • CHEMBL2071024
    • 507473-06-5
    • AVSQIANZTCVZNC-UHFFFAOYSA-N
    • DTXSID10195850
    • Ethyl4-methyl-1H-1,2,3-triazole-5-carboxylate
    • Z2037296673
    • NS00022191
    • EINECS 224-401-7
    • SCHEMBL9272935
    • AKOS016036549
    • SCHEMBL23025720
    • JT2RK3ZS7Q
    • AKOS006371671
    • 1H-1,2,3-Triazole-5-carboxylicacid,4-methyl-,ethyl ester
    • 5-Methyl-2H-1,2,3-triazole-4-carboxylic acid ethyl ester
    • DB-169141
    • G48236
    • DB-322845
    • ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate
    • Inchi: 1S/C6H9N3O2/c1-3-11-6(10)5-4(2)7-9-8-5/h3H2,1-2H3,(H,7,8,9)
    • InChI Key: AVSQIANZTCVZNC-UHFFFAOYSA-N
    • SMILES: O(C(C1C(C)=NNN=1)=O)CC

Computed Properties

  • Exact Mass: 155.06957
  • Monoisotopic Mass: 155.069
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 3
  • 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: 5
  • XLogP3: 0.6
  • Topological Polar Surface Area: 67.9A^2

Experimental Properties

  • Density: 1.242
  • Boiling Point: 287.1°Cat760mmHg
  • Flash Point: 127.5°C
  • Refractive Index: 1.522
  • PSA: 67.87
  • Vapor Pressure: 0.0±0.5 mmHg at 25°C

ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate Security Information

ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate Pricemore >>

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Additional information on ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate

Recent Advances in the Synthesis and Applications of Ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate (CAS: 4343-73-1)

Ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate (CAS: 4343-73-1) is a heterocyclic compound that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its versatile applications in drug discovery and material science. Recent studies have highlighted its potential as a key intermediate in the synthesis of bioactive molecules, including antimicrobial, anticancer, and anti-inflammatory agents. This research brief aims to provide an overview of the latest advancements related to this compound, focusing on its synthesis, mechanistic insights, and therapeutic applications.

One of the most notable developments in the synthesis of ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate involves the optimization of click chemistry protocols. Researchers have reported improved yields and selectivity using copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions, which are pivotal for constructing the triazole core. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that the use of novel copper(I) catalysts, such as Cu(I)-N-heterocyclic carbene complexes, significantly enhances the reaction efficiency, reducing side products and improving scalability for industrial applications.

In addition to synthetic advancements, ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate has been investigated for its role in the development of novel antimicrobial agents. A recent study in Bioorganic & Medicinal Chemistry Letters revealed that derivatives of this compound exhibit potent activity against multidrug-resistant bacterial strains, including methicillin-resistant Staphylococcus aureus (MRSA). The researchers attributed this activity to the compound's ability to disrupt bacterial cell wall synthesis, as evidenced by molecular docking studies and in vitro assays. These findings underscore its potential as a scaffold for designing next-generation antibiotics.

Furthermore, the compound's applications extend to cancer research. A 2024 preprint on ChemRxiv detailed the synthesis of ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate derivatives that selectively inhibit the PI3K/AKT/mTOR signaling pathway, a critical target in oncology. Preliminary in vivo studies using murine models showed promising tumor regression with minimal off-target effects, suggesting its utility in targeted cancer therapies. The study also highlighted the compound's favorable pharmacokinetic properties, such as oral bioavailability and metabolic stability, which are essential for clinical translation.

Beyond its therapeutic potential, ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate has also been explored in material science. Researchers have incorporated this compound into polymer matrices to create functional materials with tunable properties, such as fluorescence and thermal stability. A 2023 article in ACS Applied Materials & Interfaces described its use in the development of smart coatings for biomedical devices, where its triazole moiety facilitates cross-linking and enhances material durability. These innovations highlight the compound's versatility across interdisciplinary applications.

In conclusion, ethyl 5-methyl-1H-1,2,3-triazole-4-carboxylate (CAS: 4343-73-1) continues to be a focal point of research in chemical biology and medicinal chemistry. Recent studies have advanced its synthesis, elucidated its mechanistic roles in bioactive molecules, and expanded its applications in antimicrobial and anticancer therapies, as well as material science. Future research directions may include the exploration of its enantioselective synthesis and the development of hybrid molecules combining its triazole core with other pharmacophores. These efforts are expected to further solidify its position as a valuable building block in drug discovery and beyond.

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