51173-04-7 | 2-Methoxy-5-fluoropyridine

CAS:51173-04-7 | 2-Methoxy-5-fluoropyridine,Description

5-Fluoro-2-methoxypyridine is a chemical compound that is part of the broader family of substituted pyridines. These compounds are of interest due to their diverse range of applications in pharmaceuticals, agrochemicals, and materials science. The presence of both fluoro and methoxy substituents on the pyridine ring can significantly alter the compound's electronic properties, making it a valuable intermediate for various chemical syntheses.

Synthesis Analysis

The synthesis of fluoro- and methoxypyridines can be achieved through several methods. One efficient approach for synthesizing fluoropyridines involves the fluorodenitration reaction mediated by tetrabutylammonium fluoride (TBAF) under mild conditions. This method is applicable to 2- or 4-nitro-substituted pyridines and can also be extended to hydroxy- and methoxydenitration using the corresponding tetrabutylammonium species. Another synthesis route for related compounds, such as 2-amino-5-fluoropyridine, involves a series of steps including nitrification, amino acetylation, reduction of nitro, diazolization, Schiemann reaction, and hydrolysis of acetyl, which avoids the need for difficult separations and improves yield and purity.

Molecular Structure Analysis

The molecular structure of substituted pyridines can be characterized by various spectroscopic methods. For instance, the structure of 5-methoxy-2-[(E)-(6-methylpyridin-2-ylimino)methyl]phenol was elucidated using elemental analysis, UV-Vis, IR, 1H NMR, and X-ray single crystal diffraction, revealing a stable crystal structure with π-π packing and intramolecular hydrogen bonds. Similarly, the structure of related compounds can be determined to understand their conformation and electronic distribution.

Chemical Reactions Analysis

Substituted pyridines can undergo a variety of chemical reactions. For example, 5-fluoro-4-hydroxy-2-methoxypyrimidine exhibits tautomerism and can exist in solution as two oxo tautomers, with the zwitterionic tautomer being stabilized in certain solvents capable of specific solvation via hydrogen bonding. Additionally, the presence of electron-rich nitrogen and electron-deficient fluorine atoms in some fluoropyridines can lead to photoinduced electron transfer processes, which can be influenced by the presence of transition metal ions.

Physical and Chemical Properties Analysis

The physical and chemical properties of 5-fluoro-2-methoxypyridine derivatives are influenced by their substituents. For instance, the presence of a methoxy group in 5-methoxy- and 5-hydroxy-6-fluoro-1,8-naphthyridone-3-carboxylic acid derivatives indicates a tolerance that does not negatively affect biochemical potency, although only moderate whole cell antibacterial activity is observed, potentially due to poor cellular penetration. The photophysical properties of these compounds can also be studied, as seen in the case of a terpyridine-diphenylacetylene hybrid fluorophore and its metal complexes, where the fluorescence involves intramolecular charge transfer and is not affected by non-radiative relaxation processes. The photophysical properties of other related compounds, such as 5-aryl-2,2'-bipyridines, have also been investigated, showing that the incorporation of fluorine atoms can cause shifts in emission maxima and affect quantum yields.

Scientific Research Applications

Application in Cancer Research

Scientific Field: Medical Science, Oncology

Summary of the Application

5-Fluorouracil (5-FU), a derivative of 5-Fluoro-2-methoxypyridine, is widely used to treat cancer. It is used in more than 2 million cancer patients each year.

Methods of Application: The methods for 5-FU synthesis include the incorporation of radioactive and stable isotopes to study 5-FU metabolism and biodistribution.

Results or Outcomes: Beyond the well-established role for inhibiting thymidylate synthase (TS) by the 5-FU metabolite 5-fluoro-2′-deoxyuridine-5′-O-monophosphate (FdUMP), recent studies have implicated new roles for RNA modifying enzymes that are inhibited by 5-FU substitution.

Application in Microbiome Research

Scientific Field: Microbiology

Methods of Application: DFM capitalises on enhanced stability and broad applicability across diverse Proteobacteria species.

Results or Outcomes: Through the application of flow cytometry, researchers successfully differentiated, quantified, and tracked a diverse six-member synthetic community under various complex conditions.

Application in Drug Synthesis

Scientific Field: Organic Chemistry

Methods of Application: The specific methods of application are not detailed in the sources, but it involves organic chemistry investigations.

Results or Outcomes: The outcomes of this application are the creation of various nucleosides like 5-fluoro-3-deazacytidine and 5-fluoro-2′-deoxy-3-deazacytidine.

Application in Personalized Medicine

Scientific Field: Medical Science, Personalized Medicine

Methods of Application: The methods for 5-FU synthesis include the incorporation of radioactive and stable isotopes to study 5-FU metabolism and biodistribution.

Results or Outcomes: Beyond the well-established role for inhibiting thymidylate synthase (TS) by the 5-FU metabolite 5-fluoro-2′-deoxyuridine-5′-O-monophosphate (FdUMP), recent studies have implicated new roles for RNA modifying enzymes that are inhibited by 5-FU substitution.

Application in Synthesis of Fluorinated Pyridines

Scientific Field: Organic Chemistry

Methods of Application: The specific methods of application are not detailed in the sources, but it involves organic chemistry investigations.

Results or Outcomes: The outcomes of this application are the creation of various fluoropyridines.

Application in Radiobiology

Scientific Field: Radiobiology

Methods of Application: The specific methods of application are not detailed in the sources, but it involves organic chemistry investigations.

Results or Outcomes: The outcomes of this application are the creation of F 18 substituted pyridines, which present a special interest as potential imaging agents for various biological applications.

Safety And Hazards

“5-Fluoro-2-methoxypyridine” is harmful by inhalation, in contact with skin, and if swallowed. It is flammable and may cause skin irritation, serious eye irritation, and respiratory irritation.

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