Cas no 4343-71-9 (2H-1,2,3-Triazole-4-carbaldehyde)

2H-1,2,3-Triazole-4-carbaldehyde is a versatile heterocyclic aldehyde featuring a triazole core with a formyl functional group at the 4-position. This compound is of significant interest in organic synthesis and medicinal chemistry due to its reactivity as a building block for constructing more complex molecular architectures. The triazole ring offers stability and hydrogen-bonding capabilities, while the aldehyde group enables diverse transformations, including condensations, nucleophilic additions, and cyclizations. Its applications span the development of pharmaceuticals, agrochemicals, and functional materials. The compound’s well-defined structure and synthetic utility make it valuable for researchers exploring click chemistry, bioconjugation, and heterocyclic derivatization.
2H-1,2,3-Triazole-4-carbaldehyde structure
4343-71-9 structure
Product Name:2H-1,2,3-Triazole-4-carbaldehyde
CAS No:4343-71-9
MF:C3H3N3O
MW:97.0754196643829
CID:1084005
PubChem ID:227927
Update Time:2025-05-19

2H-1,2,3-Triazole-4-carbaldehyde Chemical and Physical Properties

Names and Identifiers

    • 2H-1,2,3-Triazole-4-carbaldehyde
    • 1H-1,2,3-Triazole-4-carbaldehyde
    • CS-0147648
    • v-Triazole-4-carboxaldehyde
    • CHEMBL505614
    • 16681-68-8
    • MFCD12910478
    • 2H-1,2,3-Triazole-4-carboxaldehyde
    • 1H-1,2,3-Triazole-5-carbaldehyde; 1H-[1,2,3]Triazole-4-carbaldehyde; 2H-Triazole-4-carbaldehyde; NSC 20115;
    • AC-5055
    • NSC20115
    • AT36728
    • NSC 20115
    • DS-021782
    • 1,2,3-triazole-5-aldehyde
    • F13257
    • AB28395
    • 1H-[1,2,3]Triazole-4-carbaldehyde, AldrichCPR
    • AKOS006228331
    • 2H-triazole-4-carbaldehyde
    • 1H-1,2,3-Triazole-4-carbaldehyde #
    • NSC-20115
    • 1H-1,2,3-Triazole-4-carboxaldehyde
    • AKOS016000066
    • 1H-1,3-Triazole-4-carboxaldehyde
    • 1,2,3-Triazole, 4-formyl-
    • 1H-[1,2,3]Triazole-4-carbaldehyde
    • 4343-71-9
    • triazole aldehyde
    • 1H-1,2,3-TRIAZOLE-5-CARBALDEHYDE
    • DTXSID70281102
    • EN300-183420
    • Inchi: 1S/C3H3N3O/c7-2-3-1-4-6-5-3/h1-2H,(H,4,5,6)
    • InChI Key: MOLKLIYWXFEEJM-UHFFFAOYSA-N
    • SMILES: O=CC1C=NNN=1

Computed Properties

  • Exact Mass: 97.027611728g/mol
  • Monoisotopic Mass: 97.027611728g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 7
  • Rotatable Bond Count: 1
  • Complexity: 74.6
  • 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: -0.6
  • Topological Polar Surface Area: 58.6?2

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Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
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CM311146-1g
2H-1,2,3-Triazole-4-carbaldehyde
4343-71-9 95%
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$1356 2023-03-05

Additional information on 2H-1,2,3-Triazole-4-carbaldehyde

Introduction to 2H-1,2,3-Triazole-4-carbaldehyde (CAS No. 4343-71-9)

2H-1,2,3-Triazole-4-carbaldehyde, identified by the Chemical Abstracts Service Number (CAS No.) 4343-71-9, is a heterocyclic compound that has garnered significant attention in the field of pharmaceutical and chemical research. This compound belongs to the triazole class, a family of molecules known for their diverse biological activities and utility in medicinal chemistry. The presence of a carbaldimine functional group at the 4-position of the triazole ring imparts unique reactivity and makes it a valuable intermediate in synthetic chemistry.

The structural framework of 2H-1,2,3-Triazole-4-carbaldehyde consists of a five-membered aromatic ring containing two nitrogen atoms and one carbon atom, fused with a formyl group (CHO) at the 4-position. This configuration allows for multiple synthetic pathways and functionalization opportunities, making it a versatile building block in drug discovery and material science. The compound’s ability to participate in condensation reactions, nucleophilic additions, and cyclization processes underscores its importance in organic synthesis.

In recent years, 2H-1,2,3-Triazole-4-carbaldehyde has been extensively studied for its potential applications in pharmaceutical development. One of the most notable areas of research involves its use as a precursor in the synthesis of biologically active molecules. The triazole moiety is particularly interesting due to its presence in numerous FDA-approved drugs, where it contributes to antimicrobial, antifungal, and anti-inflammatory properties. The aldehyde functionality further enhances its utility by enabling further derivatization into amides, imines, and other pharmacophores.

Recent advancements in computational chemistry have highlighted the role of 2H-1,2,3-Triazole-4-carbaldehyde in designing novel therapeutic agents. Molecular modeling studies suggest that derivatives of this compound exhibit promising interactions with biological targets such as enzymes and receptors. For instance, researchers have explored its potential as an inhibitor of metabolic enzymes implicated in cancer progression. The ability to fine-tune the electronic properties of the triazole ring through substituent effects has opened new avenues for developing targeted therapies.

The synthesis of 2H-1,2,3-Triazole-4-carbaldehyde typically involves multi-step reactions starting from readily available precursors. One common synthetic route employs the condensation of hydrazine derivatives with α-halo carbonyl compounds under controlled conditions. Alternatively, palladium-catalyzed cross-coupling reactions have been utilized to construct the triazole core with high efficiency. These methods highlight the compound’s accessibility and scalability for industrial applications.

From a mechanistic perspective, 2H-1,2,3-Triazole-4-carbaldehyde serves as a key intermediate in transition-metal-catalyzed transformations. Its reactivity towards various nucleophiles allows for the construction of complex molecular architectures essential for drug development. For example, recent studies have demonstrated its use in generating tetrazole derivatives through cycloaddition reactions with nitrile oxides or azides. Such transformations are pivotal in creating libraries of compounds for high-throughput screening.

The pharmaceutical industry has shown particular interest in 2H-1,2,3-Triazole-4-carbaldehyde due to its role in developing next-generation antibiotics and antivirals. The triazole scaffold is known to disrupt microbial cell wall synthesis or inhibit viral replication mechanisms. Researchers have reported novel derivatives exhibiting enhanced efficacy against resistant strains of bacteria and viruses. These findings underscore the importance of this compound as a scaffold for future drug candidates.

Beyond pharmaceutical applications, 2H-1,2,3-Triazole-4-carbaldehyde has found utility in materials science and agrochemical research. Its ability to form stable complexes with metal ions makes it valuable in designing catalysts and sensors. Additionally, modifications to its structure have led to the development of novel herbicides and fungicides with improved environmental profiles. Such applications demonstrate the broad versatility of this heterocyclic compound.

In conclusion,2H-1,2,3-Triazole-4-carbaldehyde (CAS No. 4343-71-9) is a multifaceted compound with significant potential across multiple scientific disciplines. Its unique structural features enable diverse synthetic pathways and biological activities, making it indispensable in pharmaceutical research and industrial applications. As computational methods continue to advance our understanding of molecular interactions,2H-1,2,3-Triazole-4-carbaldehyde will undoubtedly remain at the forefront of innovation.

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