Cas no 252989-57-4 (3-Pyridinecarboxaldehyde,5-ethynyl-)

3-Pyridinecarboxaldehyde,5-ethynyl- is a versatile heterocyclic compound featuring both an aldehyde and an ethynyl functional group on a pyridine scaffold. Its structure enables diverse reactivity, making it valuable in organic synthesis, particularly in cross-coupling reactions, click chemistry, and the construction of complex molecular architectures. The ethynyl group facilitates Sonogashira and other alkyne-based couplings, while the aldehyde moiety allows for further derivatization via condensation or nucleophilic addition. This compound is useful in pharmaceutical and materials science research, where its bifunctional nature supports the development of novel ligands, polymers, and bioactive molecules. High purity and stability ensure consistent performance in synthetic applications.
3-Pyridinecarboxaldehyde,5-ethynyl- structure
252989-57-4 structure
Product Name:3-Pyridinecarboxaldehyde,5-ethynyl-
CAS No:252989-57-4
MF:C8H5NO
MW:131.131401777267
CID:246609
PubChem ID:10510886
Update Time:2025-11-02

3-Pyridinecarboxaldehyde,5-ethynyl- Chemical and Physical Properties

Names and Identifiers

    • 3-Pyridinecarboxaldehyde,5-ethynyl-
    • 3-Pyridinecarboxaldehyde, 5-ethynyl- (9CI)
    • 5-ethynylpyridine-3-carbaldehyde
    • AT34098
    • AB63411
    • Z1198312684
    • EN300-4296288
    • AKOS006306398
    • 252989-57-4
    • 5-ETHYNYLNICOTINALDEHYDE
    • SCHEMBL20489980
    • CS-0380387
    • DTXSID70440954
    • 3-PYRIDINECARBOXALDEHYDE, 5-ETHYNYL-
    • DB-207110
    • 5-ETHYNYL-3-PYRIDINECARBOXALDEHYDE
    • Inchi: 1S/C8H5NO/c1-2-7-3-8(6-10)5-9-4-7/h1,3-6H
    • InChI Key: POPXBLXAVUEVOL-UHFFFAOYSA-N
    • SMILES: O=CC1C=NC=C(C#C)C=1

Computed Properties

  • Exact Mass: 131.037113783g/mol
  • Monoisotopic Mass: 131.037113783g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 2
  • Complexity: 167
  • 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: 30?2

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Additional information on 3-Pyridinecarboxaldehyde,5-ethynyl-

Comprehensive Guide to 3-Pyridinecarboxaldehyde,5-ethynyl- (CAS No. 252989-57-4): Properties, Applications, and Market Insights

3-Pyridinecarboxaldehyde,5-ethynyl- (CAS No. 252989-57-4) is a specialized organic compound that has garnered significant attention in pharmaceutical and material science research. This pyridine derivative features an ethynyl group at the 5-position and an aldehyde functional group at the 3-position, making it a versatile building block for various synthetic applications. The compound's molecular formula is C8H5NO, with a molecular weight of 131.13 g/mol.

The unique structure of 5-ethynyl-3-pyridinecarboxaldehyde enables its use in click chemistry reactions, particularly in Huisgen cycloaddition processes. Researchers value this compound for its ability to form triazole linkages, which are crucial in drug discovery and material science. Recent studies highlight its potential in developing targeted drug delivery systems and bioconjugation techniques, aligning with current trends in personalized medicine.

In the pharmaceutical industry, 3-Pyridinecarboxaldehyde,5-ethynyl- serves as a key intermediate for synthesizing kinase inhibitors and other bioactive molecules. Its pyridine core structure mimics natural heterocycles found in many FDA-approved drugs, making it particularly valuable for medicinal chemistry applications. The compound's reactivity profile allows for efficient modifications, addressing the growing demand for structure-activity relationship (SAR) studies in drug development.

Material scientists have explored 252989-57-4 for creating advanced polymeric materials with tailored properties. The ethynyl functionality facilitates polymerization through various mechanisms, enabling the production of materials with specific electronic or mechanical characteristics. This aligns with current industry needs for smart materials in electronics and nanotechnology applications.

The global market for 5-ethynyl-3-pyridinecarboxaldehyde has shown steady growth, driven by increasing R&D investments in pharmaceutical intermediates and functional materials. Analytical reports suggest particular demand from the Asia-Pacific region, where pharmaceutical and electronics manufacturing sectors are expanding rapidly. Quality standards for this compound typically require ≥98% purity, with specialized grades available for specific applications.

From a synthetic chemistry perspective, 3-Pyridinecarboxaldehyde,5-ethynyl- offers several advantages. Its aldehyde group provides a handle for nucleophilic additions, while the ethynyl group enables metal-catalyzed coupling reactions. This dual functionality makes it valuable for constructing complex molecular architectures, particularly in combinatorial chemistry approaches that dominate modern drug discovery workflows.

Storage and handling of CAS 252989-57-4 require standard laboratory precautions. The compound should be kept in airtight containers under inert atmosphere at recommended temperatures to maintain stability. While not classified as highly hazardous, proper laboratory safety protocols should always be followed when working with this chemical, including the use of appropriate personal protective equipment.

Recent patent literature reveals growing interest in 3-Pyridinecarboxaldehyde,5-ethynyl- derivatives for various applications. Innovations include its incorporation into fluorescent probes for biological imaging and as components in organic electronic devices. These developments reflect broader trends in bioimaging technologies and flexible electronics, areas experiencing significant research activity.

Analytical characterization of 5-ethynyl-3-pyridinecarboxaldehyde typically involves techniques such as HPLC, NMR spectroscopy, and mass spectrometry. These methods ensure batch-to-batch consistency and verify the compound's structural integrity, which is critical for research and industrial applications. Advanced purification methods, including column chromatography and recrystallization, are often employed to achieve high-purity material.

The future outlook for 252989-57-4 appears promising, with potential applications emerging in biomedical engineering and renewable energy technologies. As synthetic methodologies advance, researchers anticipate new uses for this versatile building block in developing next-generation materials and therapeutic agents. The compound's adaptability positions it well to address evolving challenges in multiple scientific disciplines.

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