Cas no 450368-21-5 (6-ethynylpyridine-3-carboxylic acid)

6-Ethynylpyridine-3-carboxylic acid is a versatile heterocyclic building block featuring both an ethynyl group and a carboxylic acid functionality. Its pyridine core provides a rigid aromatic scaffold, while the ethynyl and carboxyl groups offer reactive sites for further derivatization, such as Sonogashira coupling or amide formation. This compound is particularly useful in medicinal chemistry and materials science, where its dual functionality enables the synthesis of complex molecules or conjugated polymers. Its high purity and stability make it suitable for precise synthetic applications. The compound’s structural features also facilitate its use in click chemistry and metal-organic framework (MOF) development.
6-ethynylpyridine-3-carboxylic acid structure
450368-21-5 structure
Product Name:6-ethynylpyridine-3-carboxylic acid
CAS No:450368-21-5
MF:C8H5NO2
MW:147.130801916122
MDL:MFCD11109685
CID:327784
PubChem ID:17774328
Update Time:2025-10-31

6-ethynylpyridine-3-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 3-Pyridinecarboxylicacid, 6-ethynyl-
    • 3-Pyridinecarboxylic acid, 6-ethynyl- (9CI)
    • 6-ethynylpyridine-3-carboxylic acid
    • CS-0332154
    • SCHEMBL7611057
    • PB42839
    • DTXSID80590919
    • 6-Ethynylnicotinicacid
    • EN300-69433
    • 6-ethynylnicotinic acid
    • P18107
    • MFCD11109685
    • 450368-21-5
    • PS-15708
    • AKOS006240032
    • MDL: MFCD11109685
    • Inchi: 1S/C8H5NO2/c1-2-7-4-3-6(5-9-7)8(10)11/h1,3-5H,(H,10,11)
    • InChI Key: YILQLEDPZCOECZ-UHFFFAOYSA-N
    • SMILES: OC(C1C=NC(C#C)=CC=1)=O

Computed Properties

  • Exact Mass: 147.032028402g/mol
  • Monoisotopic Mass: 147.032028402g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 2
  • Complexity: 203
  • 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: 0.7
  • Topological Polar Surface Area: 50.2?2

Experimental Properties

  • Density: 1.3±0.1 g/cm3
  • Melting Point: 129-131 °C
  • Boiling Point: 311.9±27.0 °C at 760 mmHg
  • Flash Point: 142.4±23.7 °C
  • Vapor Pressure: 0.0±0.7 mmHg at 25°C

6-ethynylpyridine-3-carboxylic acid Security Information

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Additional information on 6-ethynylpyridine-3-carboxylic acid

Introduction to 6-ethynylpyridine-3-carboxylic acid (CAS No. 450368-21-5)

6-ethynylpyridine-3-carboxylic acid, identified by its Chemical Abstracts Service (CAS) number 450368-21-5, is a versatile heterocyclic compound that has garnered significant attention in the field of pharmaceutical and chemical research. This compound belongs to the pyridine family, characterized by a nitrogen-containing aromatic ring, and incorporates an ethynyl substituent at the 6-position and a carboxylic acid group at the 3-position. The unique structural features of 6-ethynylpyridine-3-carboxylic acid make it a valuable intermediate in the synthesis of various bioactive molecules, including potential drug candidates and functional materials.

The ethynylpyridine core structure is particularly interesting due to its ability to participate in diverse chemical reactions, such as Sonogashira coupling, which is widely used in organic synthesis to form carbon-carbon bonds. The presence of the carboxylic acid moiety further enhances its reactivity, allowing for further functionalization via esterification, amidation, or polymerization processes. These properties have positioned 6-ethynylpyridine-3-carboxylic acid as a key building block in medicinal chemistry and materials science.

In recent years, there has been growing interest in 6-ethynylpyridine derivatives due to their potential applications in drug discovery. The pyridine scaffold is a common motif in many approved drugs, owing to its favorable pharmacokinetic properties and ability to interact with biological targets. For instance, studies have shown that pyridine-based compounds can modulate enzyme activity and receptor binding, making them suitable for treating a wide range of diseases, including inflammatory disorders, infectious diseases, and cancers.

One of the most compelling aspects of 6-ethynylpyridine-3-carboxylic acid is its role as a precursor in the synthesis of small-molecule inhibitors. Researchers have leveraged its reactive sites to develop compounds that target specific enzymes or receptors involved in disease pathways. Notably, recent advancements in computational chemistry have enabled the rapid design and optimization of such inhibitors using 6-ethynylpyridine-3-carboxylic acid as a starting point. These computational approaches have accelerated the drug discovery process by predicting molecular interactions and optimizing lead compounds for better efficacy and selectivity.

The carboxylic acid group of 6-ethynylpyridine-3-carboxylic acid also facilitates its incorporation into more complex molecules through conjugation with other functional groups. For example, it can be converted into esters or amides, which are common pharmacophores in drug molecules. Additionally, the ethynyl group provides a site for further modification via cross-coupling reactions, allowing chemists to tailor the structure of their derivatives for specific biological activities.

Another area where 6-ethynylpyridine-3-carboxylic acid has shown promise is in materials science. The compound’s ability to form stable polymers and copolymers has led to investigations into its use as a monomer for advanced materials. These materials could find applications in electronics, coatings, and biodegradable polymers due to their unique electronic and mechanical properties. The versatility of 6-ethynylpyridine derivatives makes them attractive for developing next-generation functional materials with tailored properties.

The synthesis of 6-ethynylpyridine-3-carboxylic acid typically involves multi-step organic transformations starting from readily available pyridine precursors. Advances in synthetic methodologies have improved the efficiency and scalability of these processes, making it more feasible to produce this compound on an industrial scale. Furthermore, green chemistry principles have been increasingly applied to these synthetic routes, reducing waste and energy consumption while maintaining high yields.

In conclusion,6-ethynylpyridine-3-carboxylic acid (CAS No. 450368-21-5) is a multifaceted compound with significant potential in pharmaceuticals and materials science. Its unique structural features enable diverse chemical modifications, making it a valuable tool for drug discovery and material development. As research continues to uncover new applications for this compound,6-ethynylpyridine derivatives are likely to play an increasingly important role in advancing scientific innovation across multiple disciplines.

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