22282-70-8 | 2-Fluoro-4-iodopyridine

CAS:22282-70-8 | 2-Fluoro-4-iodopyridine,Description

2-Fluoro-4-iodopyridine is a halogenated pyridine derivative that serves as a valuable intermediate in the synthesis of various chemical compounds, particularly in medicinal chemistry. The presence of both fluorine and iodine atoms on the pyridine ring makes it a versatile precursor for further functionalization and incorporation into more complex molecules.

Synthesis Analysis

The synthesis of fluoropyridines can be achieved through various methods. One efficient method involves the fluorodenitration reaction mediated by tetrabutylammonium fluoride (TBAF) under mild conditions, which is applicable to 2- or 4-nitro-substituted pyridines. Another approach for synthesizing fluoropyridines includes the use of halopyridinyl(4'-methoxyphenyl)iodonium tosylates, which can be prepared from iodohalopyridines and subsequently undergo selective radiofluorination. Additionally, a novel synthetic pathway leading to 4-fluoropyridines utilizes 2-fluoroallylic alcohols, which undergo a series of rearrangements and cyclizations to yield the desired fluoropyridine structures.

Molecular Structure Analysis

The molecular structure of fluoropyridines can be influenced by the substituents on the pyridine ring. For instance, the solid-state structure of a terpyridine-diphenylacetylene hybrid fluorophore shows a trans arrangement of pyridine nitrogen atoms, which is crucial for its photophysical properties. The molecular arrangement can significantly affect the electronic structure and, consequently, the reactivity and properties of the fluoropyridine derivatives.

Chemical Reactions Analysis

2-Fluoro-4-iodopyridine can undergo various chemical reactions due to the presence of reactive halogen atoms. For example, the iodine atom can participate in coupling reactions, such as the Sonogashira cross-coupling, to introduce additional substituents onto the pyridine ring. The fluorine atom, on the other hand, can be involved in nucleophilic substitution reactions, allowing for the introduction of different functional groups.

Physical and Chemical Properties Analysis

The physical and chemical properties of 2-fluoro-4-iodopyridine are influenced by the halogen atoms attached to the pyridine ring. The electron-withdrawing nature of the fluorine atom can enhance the acidity of adjacent hydrogen atoms, while the iodine atom can make the compound more susceptible to nucleophilic substitution reactions. The presence of fluorine also affects the lipophilicity and metabolic stability of the compound, making fluoropyridines particularly interesting for pharmaceutical applications. The synthesis of aminomethylated fluoropiperidines and fluoropyrrolidines demonstrates the potential of using fluorinated azaheterocycles as bifunctional building blocks for the development of new drugs.

Scientific Research Applications

Use as a Building Block in Synthetic Chemistry

• Field : Synthetic Chemistry
• Application : 2-Fluoro-4-iodopyridine is a dihalogenated heterocyclic compound that is commonly used as a molecular scaffold for active pharmaceutical ingredients (APIs) and a substrate for synthetic chemistry.

Use in the Synthesis of Herbicides and Insecticides

• Field : Agrochemicals
• Application : Fluorinated pyridines, such as 2-Fluoro-4-iodopyridine, have been used as starting materials for the synthesis of some herbicides and insecticides.

Use in the Synthesis of β-Carboline

• Field : Medicinal Chemistry
• Application : 2-Fluoro-4-iodopyridine is used as a key building block for the synthesis of β-carboline. β-carboline finds extensive applications in anti-cancer treatments, neuroenhancement, and neuroprotection.

Use as a Bulk Pharmaceutical Agent

• Field : Pharmaceutical Industry
• Application : 2-Fluoro-4-iodopyridine is used as a bulk pharmaceutical agent and intermediate for pharmaceuticals.

Use in the Synthesis of Fluorinated Pyridines

• Field : Organic Chemistry
• Application : 2-Fluoro-4-iodopyridine is used in the synthesis of fluorinated pyridines. Fluorinated pyridines have interesting and unusual physical, chemical, and biological properties owing to the presence of the strong electron-withdrawing substituent(s) in the aromatic ring.

Use in the Synthesis of F18 Substituted Pyridines

• Field : Radiobiology
• Application : 2-Fluoro-4-iodopyridine is used in the synthesis of F18 substituted pyridines for local radiotherapy of cancer and other biologically active compounds.

Safety And Hazards

2-Fluoro-4-iodopyridine is classified as a warning hazard. It can cause skin irritation (H315) and serious eye irritation (H319). Precautionary measures include washing skin thoroughly after handling, wearing protective gloves/eye protection/face protection, and rinsing cautiously with water if it gets in the eyes.

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