Cas no 1227575-36-1 (Methyl 2-fluoro-5-methylpyridine-3-carboxylate)

Methyl 2-fluoro-5-methylpyridine-3-carboxylate is a fluorinated pyridine derivative with a methyl ester functional group, commonly employed as a versatile intermediate in pharmaceutical and agrochemical synthesis. Its key structural features—the fluorine substituent at the 2-position and the methyl group at the 5-position—enhance its reactivity and selectivity in cross-coupling reactions, nucleophilic substitutions, and other transformations. The ester group further facilitates derivatization into carboxylic acids or amides. This compound is valued for its stability, purity, and compatibility with diverse reaction conditions, making it a reliable building block for developing bioactive molecules. Its precise functionalization potential supports applications in drug discovery and fine chemical manufacturing.
Methyl 2-fluoro-5-methylpyridine-3-carboxylate structure
1227575-36-1 structure
Product Name:Methyl 2-fluoro-5-methylpyridine-3-carboxylate
CAS No:1227575-36-1
MF:C8H8FNO2
MW:169.153025627136
MDL:MFCD16611612
CID:4764232
PubChem ID:74890488
Update Time:2025-06-12

Methyl 2-fluoro-5-methylpyridine-3-carboxylate Chemical and Physical Properties

Names and Identifiers

    • Methyl 2-fluoro-5-methylpyridine-3-carboxylate
    • Methyl 2-fluoro-5-methylnicotinate
    • Y3895
    • 2-Fluoro-5-methyl-nicotinic acid methyl ester
    • Methyl2-fluoro-5-methylnicotinate
    • MFCD16611612
    • AKOS027425356
    • CS-0195027
    • E91194
    • 1227575-36-1
    • MDL: MFCD16611612
    • Inchi: 1S/C8H8FNO2/c1-5-3-6(8(11)12-2)7(9)10-4-5/h3-4H,1-2H3
    • InChI Key: OFNRLVPCSZXTRF-UHFFFAOYSA-N
    • SMILES: FC1=C(C(=O)OC)C=C(C)C=N1

Computed Properties

  • Exact Mass: 169.05390666g/mol
  • Monoisotopic Mass: 169.05390666g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 174
  • 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: 1.5
  • Topological Polar Surface Area: 39.2

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Additional information on Methyl 2-fluoro-5-methylpyridine-3-carboxylate

Methyl 2-Fluoro-5-Methylpyridine-3-Carboxylate (CAS No: 1227575-36-1) - A Key Intermediate in Modern Pharmaceutical Synthesis

Methyl 2-fluoro-5-methylpyridine-3-carboxylate (CAS No: 1227575-36-1) is a highly versatile and significant intermediate in the realm of pharmaceutical chemistry. This compound, characterized by its unique structural features, has garnered considerable attention due to its utility in the synthesis of various bioactive molecules. The presence of both fluoro and methyl substituents on the pyridine ring imparts distinct electronic and steric properties, making it a valuable building block for drug discovery and development.

The chemical structure of Methyl 2-fluoro-5-methylpyridine-3-carboxylate consists of a pyridine core substituted at the 2-position with a fluorine atom and at the 5-position with a methyl group. The carboxylate ester functionality at the 3-position further enhances its reactivity, allowing for diverse chemical transformations. These structural attributes make it an attractive candidate for medicinal chemists seeking to develop novel therapeutic agents.

In recent years, the pharmaceutical industry has witnessed a surge in the use of fluorinated pyridines due to their favorable pharmacokinetic properties. The fluorine atom, being highly electronegative, can modulate the metabolic stability and binding affinity of drug molecules. This has led to an increased interest in compounds like Methyl 2-fluoro-5-methylpyridine-3-carboxylate, which serve as crucial intermediates in the synthesis of fluorinated pyridine-based drugs.

One of the most compelling applications of Methyl 2-fluoro-5-methylpyridine-3-carboxylate is in the development of kinase inhibitors. Kinases are enzymes that play a pivotal role in numerous cellular processes, and their dysregulation is often associated with various diseases, including cancer. By incorporating this compound into drug candidates, researchers aim to develop selective kinase inhibitors that can modulate signaling pathways involved in disease progression.

The utility of Methyl 2-fluoro-5-methylpyridine-3-carboxylate extends beyond kinase inhibition. It has also been employed in the synthesis of antiviral and antibacterial agents. The fluoro substituent enhances the bioavailability and metabolic stability of these drugs, while the methyl group contributes to their binding affinity. These properties make it an indispensable tool for medicinal chemists working on antiviral and antibacterial therapies.

The synthesis of Methyl 2-fluoro-5-methylpyridine-3-carboxylate involves multi-step organic transformations that require precise control over reaction conditions. Typically, it is synthesized from commercially available precursors through a series of functional group interconversions. These include halogenation, alkylation, carboxylation, and esterification steps. The efficiency and scalability of these synthetic routes are critical for industrial production, ensuring that pharmaceutical companies can access sufficient quantities of this valuable intermediate.

In addition to its pharmaceutical applications, Methyl 2-fluoro-5-methylpyridine-3-carboxylate has found utility in materials science and agrochemical research. Its unique structural features make it a suitable candidate for developing advanced materials with tailored electronic properties. Furthermore, its incorporation into agrochemical formulations has shown promise in enhancing the efficacy and environmental compatibility of crop protection agents.

The growing demand for Methyl 2-fluoro-5-methylpyridine-3-carboxylate has spurred innovation in synthetic methodologies. Researchers are continuously exploring new synthetic routes that improve yield, reduce costs, and minimize environmental impact. Advances in catalytic processes and green chemistry principles have contributed significantly to these efforts, ensuring that this compound remains readily available for various applications.

The future prospects for Methyl 2-fluoro-5-methylpyridine-3-carboxylate are promising, with ongoing research uncovering new potential uses and applications. As our understanding of biological systems continues to evolve, so too will our ability to harness this compound's unique properties for therapeutic purposes. Whether it is in the development of novel drugs or advanced materials, Methyl 2-fluoro-5-methylpyridine-3-carboxylate is poised to play a pivotal role in shaping the future of science and technology.

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