669066-93-7 | 5-broMo-3-fluoropyridine-2-carbaldehyde

CAS:669066-93-7 | 5-broMo-3-fluoropyridine-2-carbaldehyde,Description

Synthesis Analysis

The synthesis of halogenated pyridines often involves halogen dance reactions, lithiation followed by trapping with electrophiles, or palladium-catalyzed reactions. For instance, a related compound, 5-bromo-2-chloro-4-fluoro-3-iodopyridine, was synthesized using halogen dance reactions, which could be a potential method for synthesizing 5-Bromo-3-fluoropyridine-2-carbaldehyde as well. Additionally, the chemoselective functionalization of a similar compound, 5-bromo-2-chloro-3-fluoropyridine, was achieved through catalytic amination conditions, suggesting that the bromo and fluoro substituents on the pyridine ring can be selectively manipulated.

Molecular Structure Analysis

The molecular structure of halogenated pyridines can be characterized by spectroscopic methods, X-ray crystallography, and computational methods such as DFT. For example, the crystal structure and intermolecular interactions of a bromo-indole derivative were analyzed using Hirshfeld surface and DFT calculations. These techniques could be applied to 5-Bromo-3-fluoropyridine-2-carbaldehyde to determine its molecular geometry, electronic structure, and potential intermolecular interactions.

Chemical Reactions Analysis

Halogenated pyridines participate in various chemical reactions, including cyclocondensation, amination, and substitution reactions. The presence of a carbaldehyde group in 5-Bromo-3-fluoropyridine-2-carbaldehyde suggests that it could undergo condensation reactions with amines or hydrazines to form Schiff bases or hydrazones10 . Additionally, the bromo and fluoro substituents could be involved in nucleophilic aromatic substitution (SNAr) reactions, as demonstrated by the selective functionalization of bromo-chloro-fluoropyridines.

Physical and Chemical Properties Analysis

The physical and chemical properties of 5-Bromo-3-fluoropyridine-2-carbaldehyde can be inferred from related compounds. Halogenated pyridines generally exhibit good thermal stability, as shown by the thermal analysis of a bromo-indole derivative. The presence of electronegative halogens and a carbonyl group is likely to influence the compound's polarity, solubility, and reactivity. The electronic and optical properties, such as charge transfer and molecular electrostatic potential, can be studied using frontier molecular orbital analysis and molecular docking studies.

Scientific Research Applications

Synthesis of 3-Fluoropyrroles

5-Bromo-3-fluoropyridine-2-carbaldehyde plays a role in the synthesis of 3-fluoropyrroles. It is used in the preparation of various 3-fluorinated pyrroles, which are essential in the development of new pharmaceutical compounds and materials (Surmont et al., 2009).

Chemoselective Amination

This compound is involved in chemoselective functionalization processes. Specifically, its amination under certain conditions allows for selective substitution, which is crucial in the synthesis of complex organic molecules (Stroup et al., 2007).

Synthesis of Disubstituted Fluoropyridines

It is also key in the versatile synthesis of 3,5-disubstituted 2-fluoropyridines and 2-pyridones. These compounds have significant implications in medicinal chemistry and the development of new drugs (Sutherland & Gallagher, 2003).

Cyclization Reactions

In cyclization reactions, 5-Bromo-3-fluoropyridine-2-carbaldehyde is used to create complex structures like 3-oxo-1,3-dihydrofuro[3,4-c]pyridine-1-yl alkanoates. These reactions are fundamental in organic synthesis and drug development (Cho & Kim, 2008) .

Crystallographic Studies

The compound also finds applications in crystallographic studies, helping in understanding molecular structures, which is vital in the design of new materials and drugs (Ali et al., 2005).

Safety And Hazards

This compound is classified as harmful if swallowed, causes skin irritation, may cause respiratory irritation, and causes serious eye damage. Precautionary measures include avoiding breathing dust/fume/gas/mist/vapours/spray, wearing protective gloves/clothing/eye protection/face protection, and seeking medical advice if you feel unwell.

Future Directions

While specific future directions for the use of 5-Bromo-3-fluoropyridine-2-carbaldehyde are not mentioned in the retrieved papers, its potential applications in various fields of research, such as the development of new pharmaceuticals and materials, are vast due to its reactivity and the variety of reactions it can participate in.

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