80392-79-6 | 3-Bromo-2,6-difluoropyridine

CAS:80392-79-6 | 3-Bromo-2,6-difluoropyridine,Description

3-Bromo-2,6-difluoropyridine is a halogenated pyridine derivative that has been the subject of various studies due to its potential applications in organic synthesis and pharmaceutical chemistry. The presence of bromine and fluorine atoms on the pyridine ring makes it a versatile intermediate for further chemical transformations.

Synthesis Analysis

The synthesis of halogenated pyridine derivatives often involves carbon-carbon coupling reactions. For instance, 3-bromo-5-(2,5-difluorophenyl)pyridine, a related compound, was synthesized via carbon-carbon coupling and characterized using X-ray diffraction (XRD) and spectroscopic techniques. Another approach reported the synthesis of 3-bromo-5,6-dihydropyridin-2-ones starting from α-bromoketenes and imines, showcasing the versatility of brominated pyridines in cycloaddition reactions.

Molecular Structure Analysis

The molecular structure of brominated pyridines has been studied using single-crystal X-ray diffraction data. For example, the structure of 6-bromo-2-(furan-2-yl)-3-(prop-2-ynyl)-3H-imidazo[4,5-b]pyridine was investigated to understand the molecular geometry and intermolecular interactions in the solid state. These studies are crucial for understanding the reactivity and properties of such compounds.

Chemical Reactions Analysis

Brominated pyridines participate in various chemical reactions due to the presence of a reactive bromine atom. For example, the bromine atom on the double bond of 3-bromo-5,6-dihydropyridin-2-ones allows for subsequent aziridination or bromine displacement with an amine. Additionally, the reactivity of brominated pyridines has been explored through the reactions of bromonium ions with acceptor olefins, demonstrating the potential of these compounds in synthetic chemistry.

Physical and Chemical Properties Analysis

The physical and chemical properties of brominated pyridines have been extensively studied using spectroscopic methods and density functional theory (DFT). Vibrational spectral studies provide insights into the molecular vibrations and hydrogen bonding present in these compounds. DFT calculations have been used to analyze the molecular stability, bond strength, and electronic properties, such as HOMO-LUMO energies and molecular electrostatic potential (MEP). These studies are essential for predicting the behavior of these compounds in various chemical environments.

Scientific Research Applications

• Agricultural and Pharmaceutical Applications

  • Field : Agriculture and Pharmaceuticals
  • Application : In the search for new agricultural products having improved physical, biological, and environmental properties, one of the most generally useful chemical modifications is the introduction of fluorine atoms into lead structures. About 10% of the total sales of pharmaceuticals currently used for medical treatment are drugs containing a fluorine atom.
  • Method : Fluorine-containing substituents are most commonly incorporated into carbocyclic aromatic rings, and a large number of compounds possessing fluorine-containing substituents on aryl rings have been commercialized as agricultural active ingredients.
  • Results : Over 50 years, many fluorinated medicinal and agrochemical candidates have been discovered and the interest toward development of fluorinated chemicals has been steadily increased.

• Synthesis of Herbicides and Insecticides

  • Field : Agricultural Chemistry
  • Application : Fluoropyridines, including 3-Bromo-2,6-difluoropyridine, have been used as starting materials for the synthesis of some herbicides and insecticides.
  • Method : The specific methods of synthesis would depend on the particular herbicide or insecticide being produced.
  • Results : The resulting fluorinated herbicides and insecticides often exhibit improved physical, biological, and environmental properties.

• Synthesis of Biologically Active Compounds

  • Field : Medicinal Chemistry
  • Application : Fluoropyridines are used in the synthesis of various biologically active compounds. This includes the synthesis of F18-substituted pyridines, which present a special interest as potential imaging agents for various biological applications.
  • Method : The specific methods of synthesis would depend on the particular biologically active compound being produced.
  • Results : The resulting fluorinated compounds often exhibit interesting and unusual physical, chemical, and biological properties.

• Preparation of Poly(pyridine ether)s

  • Field : Polymer Chemistry
  • Application : 2,6-Difluoropyridine, a compound similar to 3-Bromo-2,6-difluoropyridine, has been used in the preparation of poly(pyridine ether)s.
  • Method : This involves the polycondensation of bistrimethylsilyl derivatives of various diphenols with 2,6-difluoropyridine in N-methylpyrrolidone in the presence of K2CO3.
  • Results : The resulting poly(pyridine ether)s could have various applications in the field of materials science.
• Synthesis of Radiobiology Compounds
  • Field : Radiobiology
  • Application : Methods for synthesis of F 18 substituted pyridines for local radiotherapy of cancer and other biological active compounds are also presented.
  • Method : The specific methods of synthesis would depend on the particular radiobiology compound being produced.
  • Results : The resulting F 18 substituted pyridines present a special interest as potential imaging agents for various biological applications.

Safety And Hazards

3-Bromo-2,6-difluoropyridine is harmful by inhalation, in contact with skin, and if swallowed. It is recommended to avoid dust formation, breathing mist, gas or vapors, and contact with skin and eyes. Suitable personal protective equipment, including approved mask/respirator, suitable gloves/gauntlets, suitable protective clothing, and suitable eye protection, should be used when handling this compound.

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