206278-27-5 | 2-bromo-3-fluoropyrazine

CAS:206278-27-5 | 2-bromo-3-fluoropyrazine,Description

2-Bromo-3-fluoropyrazine is a halogenated pyrazine derivative, which is a class of compounds that have garnered interest in the field of medicinal chemistry and materials science due to their unique chemical properties and potential applications. While the provided papers do not directly discuss 2-Bromo-3-fluoropyrazine, they do provide insights into the chemistry of related halogenated pyrazines and pyridines, which can be used to infer the properties and reactivity of 2-Bromo-3-fluoropyrazine.

Synthesis Analysis

The synthesis of halogenated pyrazines and pyridines often involves halogen dance reactions, lithiation followed by trapping with electrophiles, and palladium-catalyzed amination reactions. For instance, 5-bromo-2-chloro-4-fluoro-3-iodopyridine was synthesized using halogen dance reactions, and its magnesiation followed by trapping with electrophiles generated various pentasubstituted pyridines. Similarly, 2-amino-5-[18F]fluoropyridines were synthesized via a palladium-catalyzed amination sequence from anisyl(2-bromopyridinyl)iodonium triflate. These methods could potentially be adapted for the synthesis of 2-Bromo-3-fluoropyrazine.

Molecular Structure Analysis

The molecular structure of halogenated pyrazines is characterized by the presence of nitrogen atoms in the ring and the substitution of hydrogen atoms by halogens, which can significantly influence the electronic properties of the molecule. For example, the structure of 5,6-di(2-fluoro-2,2-dinitroethoxy)-2,3-dicyanopyrazine was fully characterized by various spectroscopic methods, and its crystal structure was analyzed using low-temperature X-ray diffraction. These techniques could be employed to analyze the molecular structure of 2-Bromo-3-fluoropyrazine.

Chemical Reactions Analysis

Halogenated pyrazines and pyridines can undergo a variety of chemical reactions, including nucleophilic substitution, which can be used to introduce different functional groups into the molecule. For example, fluoropyrazine underwent nucleophilic reactions to form hydroxy, amino, and other substituted pyrazines. The chemoselective functionalization of halopyridines has also been demonstrated, where different conditions led to selective substitution at different positions on the pyridine ring. These findings suggest that 2-Bromo-3-fluoropyrazine could also participate in similar chemical reactions.

Physical and Chemical Properties Analysis

The physical and chemical properties of halogenated pyrazines are influenced by their molecular structure. For instance, 2,5-diamino-3,6-dicyanopyrazine exhibited strong yellowish-green fluorescence in solution, and its fluorescence properties were modified by alkylation and acylation of the amino groups. The thermal stability and energetic properties of halogenated pyrazines have also been studied, with some compounds showing excellent thermal stability and detonation performance. These properties are important for the potential applications of 2-Bromo-3-fluoropyrazine in materials science and as an intermediate in organic synthesis.

Scientific Research Applications

Radiosynthesis of Fluorinated Compounds

The synthesis of 2-amino-5-[18F]fluoropyridines through a palladium-catalyzed reaction with various amines, utilizing 2-bromo-5-[18F]fluoropyridine as a precursor, represents a significant application in the development of radiotracers for positron emission tomography (PET) imaging. This process highlights the utility of 2-Bromo-3-fluoropyrazine derivatives in radiosynthesis, facilitating the production of compounds for medical imaging and diagnostic purposes (Pauton et al., 2019).

Synthesis of Disubstituted Fluoropyridines

In another research avenue, the versatile synthesis of 3,5-disubstituted 2-fluoropyridines and 2-pyridones from 5-bromo-2-fluoro-3-pyridylboronic acid demonstrates the role of 2-Bromo-3-fluoropyrazine derivatives in facilitating the creation of complex pyridine structures. These compounds are valuable in various chemical syntheses, serving as intermediates for further chemical transformations (Sutherland & Gallagher, 2003).

Copper-Catalyzed Arylation

The copper-catalyzed N-arylation of 3-alkoxypyrazoles using bromopyridines, including derivatives of 2-Bromo-3-fluoropyrazine, underlines the adaptability of these compounds in constructing pyridine isomers. This method enhances the diversity of chemical entities available for further pharmaceutical and chemical research, illustrating the compound's utility in facilitating novel syntheses (Guillou et al., 2010).

Chemoselective Amination

The chemoselective amination of 5-bromo-2-chloro-3-fluoropyridine showcases the precise functionalization possible with 2-Bromo-3-fluoropyrazine derivatives. This specificity in reaction pathways allows for targeted modifications, enabling the synthesis of compounds with tailored properties for pharmaceutical applications (Stroup et al., 2007).

Development of Fluorosulfonylvinylation Methods

The development of a clickable connective hub based on 1-bromo-2-triazolethane-1-sulfonyl fluoride highlights innovative approaches to introducing functional groups into primary and secondary amines, including pharmaceuticals. This application underscores the potential of 2-Bromo-3-fluoropyrazine derivatives in the development of new chemical methodologies for the creation of bioactive molecules with enhanced properties (Leng et al., 2020).

Safety And Hazards

The compound has been assigned the GHS07 pictogram, with the signal word "Warning". Hazard statements include H227, H302, H315, H319, and H335. Precautionary statements include P210, P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501.

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