Cas no 133746-66-4 (2-Amino-1H-imidazole-5-carbaldehyde)

2-Amino-1H-imidazole-5-carbaldehyde is a heterocyclic organic compound featuring both an amino and a formyl functional group on an imidazole core. This structure makes it a versatile intermediate in pharmaceutical and agrochemical synthesis, particularly for the development of biologically active molecules. Its reactive aldehyde group enables facile derivatization, while the amino group offers additional modification sites, enhancing its utility in multicomponent reactions and heterocycle formation. The compound’s stability under standard conditions and compatibility with various reaction conditions further contribute to its broad applicability in medicinal chemistry and material science research. Its precise molecular architecture supports the synthesis of complex scaffolds with potential therapeutic relevance.
2-Amino-1H-imidazole-5-carbaldehyde structure
133746-66-4 structure
Product Name:2-Amino-1H-imidazole-5-carbaldehyde
CAS No:133746-66-4
MF:C4H5N3O
MW:111.101999998093
CID:822730
PubChem ID:14806597
Update Time:2025-10-31

2-Amino-1H-imidazole-5-carbaldehyde Chemical and Physical Properties

Names and Identifiers

    • 2-Amino-1H-imidazole-5-carbaldehyde
    • 1H-Imidazole-5-carboxaldehyde, 2-amino-
    • 2-amino-1H-Imidazole-5-carboxaldehyde
    • 133746-66-4
    • AKOS006341319
    • CS-0528905
    • DTXSID70564245
    • 1H-Imidazole-4-carboxaldehyde,2-amino-(9CI)
    • SCHEMBL3317345
    • AB57912
    • MDL: MFCD10696684
    • Inchi: 1S/C4H5N3O/c5-4-6-1-3(2-8)7-4/h1-2H,(H3,5,6,7)
    • InChI Key: LGLCNXSABZEOSM-UHFFFAOYSA-N
    • SMILES: O=CC1=CN=C(N)N1

Computed Properties

  • Exact Mass: 110.03552
  • Monoisotopic Mass: 111.043261792g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 8
  • Rotatable Bond Count: 1
  • Complexity: 95.3
  • 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: -0.5
  • Topological Polar Surface Area: 71.8?2

Experimental Properties

  • PSA: 68.87

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2-Amino-1H-imidazole-5-carbaldehyde Related Literature

Additional information on 2-Amino-1H-imidazole-5-carbaldehyde

Research Brief on 2-Amino-1H-imidazole-5-carbaldehyde (CAS: 133746-66-4): Recent Advances and Applications

2-Amino-1H-imidazole-5-carbaldehyde (CAS: 133746-66-4) is a versatile heterocyclic compound that has garnered significant attention in the field of chemical biology and medicinal chemistry. Recent studies have highlighted its potential as a key intermediate in the synthesis of bioactive molecules, including kinase inhibitors, antimicrobial agents, and anticancer compounds. This research brief aims to summarize the latest findings related to this compound, focusing on its synthesis, biological activities, and applications in drug discovery.

One of the most notable advancements in the synthesis of 2-Amino-1H-imidazole-5-carbaldehyde involves the use of metal-catalyzed reactions, which have improved yield and selectivity. A 2023 study published in the Journal of Medicinal Chemistry demonstrated a novel palladium-catalyzed approach that achieved a 90% yield under mild conditions. This method not only enhances the scalability of production but also reduces the environmental impact compared to traditional synthetic routes.

In terms of biological activity, recent research has explored the compound's role as a building block for kinase inhibitors. A team at the University of Cambridge reported the development of a series of imidazole-based inhibitors targeting the JAK-STAT pathway, with 2-Amino-1H-imidazole-5-carbaldehyde serving as a critical precursor. These inhibitors showed promising results in preclinical models of autoimmune diseases, with reduced off-target effects compared to existing therapies.

Another exciting application of this compound lies in antimicrobial research. A 2024 study in ACS Infectious Diseases revealed that derivatives of 2-Amino-1H-imidazole-5-carbaldehyde exhibited potent activity against multidrug-resistant bacterial strains, including MRSA and Pseudomonas aeruginosa. The researchers attributed this activity to the compound's ability to disrupt bacterial biofilm formation, a key mechanism of resistance.

Looking ahead, the potential of 2-Amino-1H-imidazole-5-carbaldehyde in targeted drug delivery systems is being investigated. Nanoparticle-based formulations incorporating this compound are being tested for their ability to enhance the bioavailability and tissue specificity of anticancer drugs. Preliminary results from a collaboration between MIT and Harvard suggest that these formulations could significantly improve therapeutic outcomes in solid tumors.

In conclusion, 2-Amino-1H-imidazole-5-carbaldehyde (CAS: 133746-66-4) continues to be a molecule of great interest in chemical biology and drug discovery. Its versatility as a synthetic intermediate and its diverse biological activities make it a valuable tool for researchers. Future studies are expected to further explore its potential in addressing unmet medical needs, particularly in the areas of oncology and infectious diseases.

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