18614-51-2 | 4-Amino-2-fluoropyridine

CAS:18614-51-2 | 4-Amino-2-fluoropyridine,Description

4-Amino-2-fluoropyridine is a compound of interest in the field of chemistry due to its potential applications in pharmaceuticals and material science. It is a fluorinated pyridine derivative, which means it contains a pyridine ring—a six-membered aromatic ring with one nitrogen atom—substituted with a fluorine atom and an amino group at specific positions. The presence of fluorine is particularly noteworthy as it can significantly alter the physical, chemical, and biological properties of organic compounds, making them valuable in drug design and development.

Synthesis Analysis

The synthesis of fluorinated pyridines, including 4-amino-2-fluoropyridine, has been a subject of various studies. One approach to synthesizing related fluorinated azaheterocycles involves the regioselective bromofluorination of N-Boc-protected methylenepiperidine and methylenepyrrolidine. Another method for synthesizing 2-aminopyridine derivatives, which could be adapted for 4-amino-2-fluoropyridine, uses nucleophilic substitution and hydrolysis of 2-fluoropyridine and acetamidine hydrochloride under catalyst-free conditions. Additionally, a novel pathway for 4-fluoropyridines has been reported, which could potentially be applied to the synthesis of 4-amino-2-fluoropyridine, involving Ireland-Claisen and aza-Cope rearrangements.

Molecular Structure Analysis

The molecular structure of 4-amino-2-fluoropyridine and its derivatives has been explored in several studies. For instance, the reaction of 4-amino-2-fluoropyridine with copper halides has led to the formation of neutral coordination complexes with interesting geometries and magnetic properties. These complexes have been characterized by X-ray crystallography, revealing distorted square planar and tetrahedral geometries.

Chemical Reactions Analysis

4-Amino-2-fluoropyridine can participate in various chemical reactions due to its reactive amino group and the electron-withdrawing effect of the fluorine atom. The fluorine atom can activate the pyridine ring towards nucleophilic substitution reactions, as demonstrated in the selective fluorination of 4-substituted 2-aminopyridines. Moreover, the amino group can be involved in the formation of coordination complexes, as seen in the synthesis of copper(II) halide complexes.

Physical and Chemical Properties Analysis

The physical and chemical properties of 4-amino-2-fluoropyridine are influenced by the presence of the amino and fluorine substituents. The fluorine atom is highly electronegative, which can affect the acidity, basicity, and hydrogen bonding capabilities of the molecule. The amino group can act as a hydrogen bond donor or acceptor, which can impact the solubility and reactivity of the compound. The synthesis of related fluorinated compounds, such as 3-[18F]fluoro-4-aminopyridine, has been investigated for use in PET imaging, indicating the importance of understanding the physical and chemical properties of these molecules.

Scientific Research Applications

• Organic Synthesis

  • Summary of Application : 4-Amino-2-fluoropyridine is an important raw material and intermediate used in organic synthesis. It’s used to create a variety of complex organic compounds.

• Agrochemical Industry

  • Summary of Application : 4-Amino-2-fluoropyridine is used in the agrochemical industry. It’s used in the synthesis of various agrochemicals.

• Pharmaceutical Industry

  • Summary of Application : 4-Amino-2-fluoropyridine is used in the pharmaceutical industry. It’s used in the synthesis of various pharmaceuticals.

• Dyestuff Field

  • Summary of Application : 4-Amino-2-fluoropyridine is used in the dyestuff field. It’s used in the synthesis of various dyes.

• Synthesis of Fluorinated Pyridines

  • Summary of Application : 4-Amino-2-fluoropyridine 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.
  • Methods of Application : The specific methods of application can vary widely depending on the desired end product. Generally, it involves reactions under controlled conditions with various reagents.
  • Results or Outcomes : The outcomes also depend on the specific reactions being carried out. In general, the use of 4-Amino-2-fluoropyridine can help to synthesize a wide range of fluorinated pyridines.

• Synthesis of Trifluoromethylpyridines

  • Summary of Application : 4-Amino-2-fluoropyridine is used in the synthesis of trifluoromethylpyridines. Trifluoromethylpyridines are an important subgroup of fluorinated compounds and have found applications in the agrochemical, pharmaceutical, and functional materials fields.
  • Methods of Application : The compound is used as an intermediate in the synthesis of various trifluoromethylpyridines. The specific methods of application can vary widely.
  • Results or Outcomes : The use of 4-Amino-2-fluoropyridine in the synthesis of trifluoromethylpyridines can result in products with improved physical, biological, and environmental properties.

• Synthesis of URAT-1 Inhibitors and Central System Disorder Drugs

  • Summary of Application : 4-Amino-2-fluoropyridine is used as a novel medical intermediate, widely applied to URAT-1 inhibitors and central system disorder drugs. It’s also an important intermediate of a plurality of inhibitors such as tyrosine kinase inhibitors, PI3K inhibitors, aldosterone synthase inhibitors, and the like.
  • Methods of Application : The compound is used as an intermediate in the synthesis of various inhibitors. The specific methods of application can vary widely.
  • Results or Outcomes : The use of 4-Amino-2-fluoropyridine in the synthesis of these inhibitors can result in drugs with improved efficacy and safety profiles.

• Synthesis of Fluorinated Compounds in Agrochemical, Pharmaceutical, and Functional Materials Fields

  • Summary of Application : Many recent advances in the agrochemical, pharmaceutical, and functional materials fields have been made possible by the development of organic compounds containing fluorine. Indeed, the effects of fluorine and fluorine-containing moieties on the biological activities and physical properties of compounds have earned fluorine a unique place in the arsenal of the discovery chemist.
  • Methods of Application : The compound is used as an intermediate in the synthesis of various fluorinated compounds. The specific methods of application can vary widely.
  • Results or Outcomes : The use of 4-Amino-2-fluoropyridine in the synthesis of these fluorinated compounds can result in products with improved physical, biological, and environmental properties.

Safety And Hazards

4-Amino-2-fluoropyridine may cause respiratory irritation, is harmful if swallowed, causes skin irritation, and causes serious eye irritation. It is recommended to handle it in a well-ventilated place, wear suitable protective clothing, and avoid contact with skin and eyes.

Future Directions

Fluoropyridines, including 4-Amino-2-fluoropyridine, are of increasing interest due to their interesting and unusual physical, chemical, and biological properties. They are being explored for use in various biological applications, including as potential imaging agents.

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