84476-99-3 | 2,5-Difluoropyridine

CAS:84476-99-3 | 2,5-Difluoropyridine,Description

2,5-Difluoropyridine is a fluorinated pyridine derivative that is of interest due to its potential applications in various fields, including medicinal chemistry and materials science. The presence of fluorine atoms can significantly alter the physical and chemical properties of a molecule, making it a valuable compound for further functionalization and synthesis of complex molecules.

Synthesis Analysis

The synthesis of fluorinated pyridines, such as 2,5-difluoropyridine, often involves regioselective metalation and subsequent carboxylation. Protective groups like chlorine or trimethylsilyl are used to achieve regioexhaustive substitution at each vacant position of the pyridine ring. This method allows for the derivation of several fluorinated pyridinecarboxylic acids from the starting material. Additionally, the synthesis of related compounds, such as 2,3-difluoro-5-chloropyridine, has been achieved using potassium fluoride as a fluorination agent in the presence of a phase transfer catalyst, demonstrating the versatility of fluorination reactions.

Molecular Structure Analysis

The molecular structure of fluorinated pyridines is characterized by the presence of fluorine atoms on the pyridine ring, which can influence the electronic distribution and reactivity of the molecule. For instance, the crystal structure of a related compound, the interaction product of 5-trifluoromethyl-pyridine-2-thione with iodine, shows a complex with linear anions and cationic moieties linked by hydrogen bonds, illustrating the impact of fluorine on the molecular geometry.

Chemical Reactions Analysis

Fluorinated pyridines participate in various chemical reactions, which are often influenced by the presence of fluorine atoms. For example, 2-(trifluoromethylsulfonyloxy)pyridine (TFOP) has been used as a reagent for ketone synthesis from carboxylic acids and aromatic hydrocarbons, demonstrating the utility of fluorinated pyridines in facilitating acylation reactions. Moreover, the reactivity of 2,5-difluoropyridine can be exploited for the synthesis of novel electron acceptors, as seen in the formation of a charge-transfer complex with 4-(dimethylamino)pyridine.

Physical and Chemical Properties Analysis

The physical and chemical properties of 2,5-difluoropyridine are influenced by the electronegativity and small size of the fluorine atoms. These properties can lead to increased stability and reactivity in certain chemical environments. The toxicity profile of related compounds, such as 5-amino-2-(trifluoromethyl)pyridine, has been studied, revealing that these compounds can be toxic and should be handled with caution in industrial applications. The electron-withdrawing effect of fluorine also contributes to the high reduction potential of fluorinated electron acceptors, which is significant for their use in electronic applications.

Scientific Research Applications

Synthesis of Fluorinated Pyridines

• Scientific Field: Chemistry
• Application Summary: 2,5-Difluoropyridine is used in the synthesis of fluorinated pyridines. Fluoropyridines have interesting and unusual physical, chemical, and biological properties due to the presence of strong electron-withdrawing substituents in the aromatic ring. They have reduced basicity and are usually less reactive than their chlorinated and brominated analogues.
• Methods of Application: The methods of synthesis of 2-, 3-, 4-fluoropyridines, di-, tri-, polyfluoropyridines, perfluoroalkylpyridines, and also fluoropyridines fused with carbo-, heterocycles are presented. Specific methods include the Umemoto reaction and Balts-Schiemann reaction.

Preparation of Poly(Pyridine Ether)s

• Scientific Field: Polymer Chemistry
• Application Summary: 2,5-Difluoropyridine has been used in the preparation of poly(pyridine ether)s via polycondensation with silylated 1,1,1-tris(4-hydroxyphenyl)ethane.
• Methods of Application: The polycondensation of bistrimethylsilyl derivatives of various diphenols with 2,5-Difluoropyridine in N-methylpyrrolidone in the presence of K2CO3 has been investigated.
• Results or Outcomes: The results of this application are not specified in the source.

Synthesis of Medicinal Raw Material

• Scientific Field: Medicinal Chemistry
• Application Summary: 2,5-Difluoropyridine is used as a starting material in the synthesis of many pharmaceuticals, particularly as an important intermediate of a lot of pyridine compounds.
• Methods of Application: The synthesis method involves preparing 2,5-dibromopyridine from 2,5-dichloropyridine through a halogenation technology, and then carrying out a methylation reaction to obtain 2,5-difluoropyridine.
• Results or Outcomes: The synthesis method of the medicinal raw material 2,5-difluoropyridine has the advantages of simplicity, high efficiency, safe operation, and high practicality in concrete production.

Synthesis of Herbicides and Insecticides

• Scientific Field: Agrochemistry
• Application Summary: 2,5-Difluoropyridine is used as a starting material for the synthesis of some herbicides and insecticides.
• Methods of Application: The specific methods of synthesis are not specified in the source.
• Results or Outcomes: The results of this application are not specified in the source.

Synthesis of F18 Substituted Pyridines

• Scientific Field: Radiobiology
• Application Summary: 2,5-Difluoropyridine is used in the synthesis of F18 substituted pyridines for local radiotherapy of cancer and other biological active compounds.
• Methods of Application: The specific methods of synthesis are not specified in the source.
• Results or Outcomes: The results of this application are not specified in the source.

Synthesis of Benzofuropyridines

• Scientific Field: Organic Chemistry
• Application Summary: 2,5-Difluoropyridine is used in the synthesis of benzofuropyridines.
• Methods of Application: The specific methods of synthesis are not specified in the source.
• Results or Outcomes: The results of this application are not specified in the source.

Safety And Hazards

2,5-Difluoropyridine is considered hazardous. It is a flammable liquid and vapor. It can cause skin irritation, serious eye irritation, and may cause respiratory irritation. Safety measures include washing face, hands, and any exposed skin thoroughly after handling, wearing protective gloves/clothing/eye protection/face protection, avoiding breathing dust/fume/gas/mist/vapors/spray, and using only outdoors or in a well-ventilated area.

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