210169-13-4 | 2,6-dibroMo-3,5-difluoropyridine

CAS:210169-13-4 | 2,6-dibroMo-3,5-difluoropyridine,Description

2,6-Dibromo-3,5-difluoropyridine is a polyhalogenated heterocyclic compound that has been the subject of various studies due to its interesting chemical properties and potential applications. The compound is characterized by the presence of bromine and fluorine atoms on a pyridine ring, which significantly influences its reactivity and interactions with other molecules.

Synthesis Analysis

The synthesis of halogenated pyridine derivatives, including those similar to 2,6-dibromo-3,5-difluoropyridine, often involves carbon-carbon coupling reactions, which are a cornerstone in the field of organic chemistry. Lithiation reactions have also been employed to prepare functionalized pyridine derivatives from tribromofluoropyridines, indicating the versatility of these compounds in synthetic chemistry.

Molecular Structure Analysis

X-ray crystallography has been used to determine the molecular structures of related dihalopyridines. For instance, 2,6-dibromo-3,5-dimethylpyridine exhibits a racemic twin with two symmetry-independent molecules in the asymmetric unit, while 2,6-diiodo-3,5-dimethylpyridine shows a non-planar saddle-shaped pyridine ring. These studies highlight the influence of halogen substituents on the geometry and solid-state packing of the pyridine ring.

Chemical Reactions Analysis

The reactivity of halogenated pyridines is significantly affected by the presence and position of the halogen substituents. For example, nucleophilic substitution in difluoro- and trifluoropyridines typically occurs at the 4-position, but with certain modifications, such as the introduction of a trialkylsilyl group, the substitution can be redirected to the 2- or 6-position. This regiocontrol is crucial for the synthesis of various pyridine-based compounds.

Physical and Chemical Properties Analysis

The physical and chemical properties of halogenated pyridines are often studied using spectroscopic techniques and computational methods. Density functional theory (DFT) calculations have been used to analyze the vibrational spectra, molecular stability, and bond strength of compounds like 3,5-dibromopyridine and 3,5-dichloro-2,4,6-trifluoropyridine. Additionally, the effect of ortho-fluorination on intermolecular interactions has been investigated, revealing that such modifications can significantly alter the behavior of pyridine in complex formation with other molecules, such as CO2.

Scientific Research Applications

• Synthesis of Fluorinated Pyridines

  • Field : Organic Chemistry
  • Application : 2,6-Dibromo-3,5-difluoropyridine is used in the synthesis of fluorinated pyridines. Fluoropyridines have reduced basicity and are usually less reactive than their chlorinated and brominated analogues.
  • Method : The methods of synthesis of 2-, 3-, 4-fluoropyridines, di-, tri-, polyfluoropyridines, perfluoroalkylpyridines and also fluoropyridines fused with carbo-, heterocycles are presented.
  • Results : The synthesis of fluorinated pyridines results in compounds with interesting and unusual physical, chemical and biological properties owing to the presence of the strong electron-withdrawing substituent (s) in the aromatic ring.

• Preparation of Poly (pyridine ether)s

  • Field : Polymer Chemistry
  • Application : 2,6-Dibromo-3,5-difluoropyridine has been used in the preparation of poly (pyridine ether)s.
  • Method : Polycondensation of bistrimethylsilyl derivatives of various diphenols with 2,6-difluoropyridine in N -methylpyrrolidone in the presence of K 2 CO 3 has been investigated.
  • Results : The result is the formation of poly (pyridine ether)s.

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Preparation