Cas no 216444-00-7 (methyl 6-ethynylpyridine-3-carboxylate)

Methyl 6-ethynylpyridine-3-carboxylate is a versatile pyridine-based building block widely used in organic synthesis and pharmaceutical research. Its structure features an ethynyl group at the 6-position and a methyl ester at the 3-position, enabling diverse functionalization through click chemistry, cross-coupling reactions, and nucleophilic substitutions. The compound serves as a key intermediate in the synthesis of heterocyclic compounds, bioactive molecules, and advanced materials. Its high reactivity, stability under standard conditions, and compatibility with various reaction conditions make it valuable for medicinal chemistry and material science applications. The ethynyl group allows efficient participation in Huisgen cycloaddition (azide-alkyne click chemistry), while the ester moiety offers further derivatization flexibility. This compound is particularly useful for constructing complex molecular architectures with precision.
methyl 6-ethynylpyridine-3-carboxylate structure
216444-00-7 structure
Product Name:methyl 6-ethynylpyridine-3-carboxylate
CAS No:216444-00-7
MF:C9H7NO2
MW:161.157382249832
MDL:MFCD16988751
CID:1109096
PubChem ID:22125933
Update Time:2025-11-01

methyl 6-ethynylpyridine-3-carboxylate Chemical and Physical Properties

Names and Identifiers

    • 6-ethynyl-3-Pyridinecarboxylic acid methyl ester
    • Methyl 6-ethynylnicotinate
    • methyl 6-ethynylpyridine-3-carboxylate
    • FRIWHMYAJZHCGW-UHFFFAOYSA-N
    • AK151766
    • 3-Pyridinecarboxylic acid, 6-ethynyl-, methyl ester
    • SCHEMBL4550568
    • MFCD16988751
    • methyl6-ethynylnicotinate
    • DTXSID90622639
    • DB-320071
    • 216444-00-7
    • DS-9633
    • CS-0043883
    • A911399
    • F19828
    • Z1122484055
    • AKOS024259464
    • EN300-1697863
    • MDL: MFCD16988751
    • Inchi: 1S/C9H7NO2/c1-3-8-5-4-7(6-10-8)9(11)12-2/h1,4-6H,2H3
    • InChI Key: FRIWHMYAJZHCGW-UHFFFAOYSA-N
    • SMILES: O(C)C(C1C=NC(C#C)=CC=1)=O

Computed Properties

  • Exact Mass: 161.047678466g/mol
  • Monoisotopic Mass: 161.047678466g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 3
  • Complexity: 216
  • 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
  • Topological Polar Surface Area: 39.2
  • XLogP3: 1

Experimental Properties

  • Boiling Point: 249.7±25.0°C at 760 mmHg

methyl 6-ethynylpyridine-3-carboxylate Security Information

  • Hazard Statement: H315-H319-H335
  • Storage Condition:Sealed in dry,Room Temperature

methyl 6-ethynylpyridine-3-carboxylate Pricemore >>

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Additional information on methyl 6-ethynylpyridine-3-carboxylate

Recent Advances in the Application of Methyl 6-Ethynylpyridine-3-Carboxylate (CAS: 216444-00-7) in Chemical Biology and Pharmaceutical Research

Methyl 6-ethynylpyridine-3-carboxylate (CAS: 216444-00-7) is a versatile chemical intermediate that has garnered significant attention in recent years due to its potential applications in chemical biology and pharmaceutical research. This compound, characterized by its ethynyl and carboxylate functional groups, serves as a key building block in the synthesis of various bioactive molecules. Recent studies have highlighted its utility in the development of novel therapeutics, particularly in the fields of oncology and neurodegenerative diseases. The unique reactivity of the ethynyl group allows for efficient conjugation with other molecules, making it a valuable tool in drug discovery and development.

One of the most notable applications of methyl 6-ethynylpyridine-3-carboxylate is its role in click chemistry, a powerful tool for bioconjugation and drug delivery. Researchers have successfully utilized this compound in the synthesis of targeted drug conjugates, where it serves as a linker between therapeutic agents and targeting moieties. For instance, a recent study published in the Journal of Medicinal Chemistry demonstrated the use of this compound in the development of antibody-drug conjugates (ADCs) for cancer therapy. The study reported improved pharmacokinetic properties and enhanced tumor targeting, underscoring the compound's potential in precision medicine.

In addition to its applications in drug delivery, methyl 6-ethynylpyridine-3-carboxylate has also been explored as a scaffold for the design of small-molecule inhibitors. A 2023 study in ACS Chemical Biology revealed that derivatives of this compound exhibit potent inhibitory activity against specific kinases involved in neurodegenerative diseases. The researchers employed structure-activity relationship (SAR) studies to optimize the compound's binding affinity and selectivity, leading to the identification of promising lead candidates for further development. These findings highlight the compound's versatility and its potential to address unmet medical needs.

Another area of research where methyl 6-ethynylpyridine-3-carboxylate has shown promise is in the field of chemical probes. Chemical probes are small molecules used to investigate biological pathways and validate drug targets. A recent publication in Nature Chemical Biology described the use of this compound in the development of a fluorescent probe for imaging protein-protein interactions in live cells. The probe's high specificity and sensitivity enabled real-time visualization of dynamic cellular processes, providing valuable insights into disease mechanisms. This application underscores the compound's utility in basic research and its potential to accelerate the discovery of new therapeutic targets.

Despite these advancements, challenges remain in the large-scale synthesis and application of methyl 6-ethynylpyridine-3-carboxylate. Issues such as stability, solubility, and cost-effectiveness need to be addressed to fully realize its potential in industrial settings. However, ongoing research efforts are focused on overcoming these limitations, with several groups reporting improved synthetic routes and formulation strategies. For example, a recent patent application disclosed a novel catalytic system for the efficient and scalable synthesis of this compound, paving the way for its broader adoption in pharmaceutical manufacturing.

In conclusion, methyl 6-ethynylpyridine-3-carboxylate (CAS: 216444-00-7) represents a promising chemical entity with diverse applications in chemical biology and pharmaceutical research. Its unique structural features and reactivity make it a valuable tool for drug discovery, targeted therapy, and basic research. As the field continues to evolve, further studies are expected to uncover new applications and optimize its use in various therapeutic contexts. The compound's potential to address critical challenges in medicine underscores the importance of continued investment in its research and development.

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