82671-03-2 | ethyl 2,6-dichloro-5-fluoropyridine-3-carboxylate

CAS:82671-03-2 | ethyl 2,6-dichloro-5-fluoropyridine-3-carboxylate,Description

Ethyl 2,6-dichloro-5-fluoropyridine-3-carboxylate is a chemical compound that serves as a key intermediate in the synthesis of various pharmacologically active molecules, including Quinolone antibacterial agents. Its structure contains a pyridine ring, a common motif in many drugs, which is substituted with chlorine and fluorine atoms at the 2, 6, and 5 positions, respectively, and an ester group at the 3 position.

Synthesis Analysis

The synthesis of Ethyl 2,6-dichloro-5-fluoropyridine-3-carboxylate has been reported to involve the treatment of 2,6-dichloro-5-fluoro-nicotinic acid with Sulphurous oxychloride to yield 2,6-dichloro-5-fluoronicotinoyl chloride, which is then reacted with a carbanion. The reaction is improved by using cost-effective materials and selecting the best reagent to produce high-quality crystals. Additionally, the decarboxylative Blaise reaction has been utilized for the efficient synthesis of related compounds, demonstrating the versatility of reactions involving this moiety.

Molecular Structure Analysis

While the specific molecular structure analysis of Ethyl 2,6-dichloro-5-fluoropyridine-3-carboxylate is not detailed in the provided papers, related compounds have been studied using X-ray diffraction crystallography, FT-IR, and NMR spectroscopy. These techniques allow for the determination of the molecular geometry, vibrational frequencies, and chemical shifts, which are essential for understanding the physical and chemical properties of the compound.

Chemical Reactions Analysis

The reactivity of Ethyl 2,6-dichloro-5-fluoropyridine-3-carboxylate and its derivatives can be inferred from the reactions of similar compounds. For instance, ethyl 6-alkyl(aryl)-4-chloromethyl-2-methylpyridine-3-carboxylates react with ammonia and primary amines to yield various substituted pyridines. These reactions highlight the potential of Ethyl 2,6-dichloro-5-fluoropyridine-3-carboxylate to undergo nucleophilic substitution and other transformations that are valuable in medicinal chemistry.

Physical and Chemical Properties Analysis

The physical and chemical properties of Ethyl 2,6-dichloro-5-fluoropyridine-3-carboxylate are closely related to its molecular structure. The presence of electronegative atoms such as chlorine and fluorine can influence the compound's polarity, solubility, and reactivity. The ester group may also affect its boiling point and reactivity towards hydrolysis. Although the specific properties are not detailed in the provided papers, related compounds have been characterized by their crystal structures, vibrational frequencies, and molecular electrostatic potential, which provide insights into their reactivity and potential applications.

Scientific Research Applications

Synthesis of Fluorinated Pyridines

• Field : Organic Chemistry
• Application : This compound is used in the synthesis of fluorinated pyridines. Fluoropyridines have reduced basicity and are usually less reactive than their chlorinated and brominated analogues. A selective synthesis of fluoropyridines remains a challenging problem.
• Method : The methods of synthesis of 2-, 3-, 4-fluoropyridines, di-, tri-, polyfluoropyridines, perfluoroalkylpyridines and also fluoropyridines fused with carbo-, heterocycles are presented. Methods for synthesis of F 18 substituted pyridines for local radiotherapy of cancer and other biological active compounds are also presented.
• Results : The synthesis of fluorinated pyridines has led to the development of new agricultural products having improved physical, biological, and environmental properties.

Preparation of Self Assembled Monolayer (SAMs) Compounds

• Field : Material Science
• Application : This compound may be used in the preparation of self-assembled monolayer (SAMs) compounds.
• Method : The specific method of application or experimental procedures for this application is not provided in the source.
• Results : The outcomes of this application are not provided in the source.

Molecular Scaffold for Fluoroquinolone Derivatives

• Field : Medicinal Chemistry
• Application : This compound is a molecular scaffold for fluoroquinolone derivatives. Fluoroquinolones are a type of antibiotic that are used to treat a variety of bacterial infections.
• Method : The specific method of application or experimental procedures for this application is not provided in the source.
• Results : The outcomes of this application are not provided in the source.

Preparation of Self Assembled Monolayer (SAMs) Compounds

• Field : Material Science
• Application : This compound may be used in the preparation of self-assembled monolayer (SAMs) compounds.
• Method : The specific method of application or experimental procedures for this application is not provided in the source.
• Results : The outcomes of this application are not provided in the source.

Molecular Scaffold for 1,8-Naphthyridine Derivatives

• Field : Medicinal Chemistry
• Application : This compound is also a molecular scaffold for 1,8-naphthyridine derivatives including Enoxacin, Trovafloxacin and Tosufloxacin. These are used to reduce the side effects of medication and expand the medical applications.
• Method : The specific method of application or experimental procedures for this application is not provided in the source.
• Results : The outcomes of this application are not provided in the source.

Safety And Hazards

The compound is labeled with the GHS07 pictogram. The hazard statements associated with it are H302-H315-H319-H335, indicating that it is harmful if swallowed, causes skin irritation, causes serious eye irritation, and may cause respiratory irritation. The precautionary statements are P261-P305+P351+P338, advising to avoid breathing dust/fume/gas/mist/vapors/spray, and if in eyes, rinse cautiously with water for several minutes and remove contact lenses if present and easy to do.

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