114776-15-7 | 2-CHLORO-4-FLUORO-5-NITROBENZOIC ACID

CAS:114776-15-7 | 2-CHLORO-4-FLUORO-5-NITROBENZOIC ACID,Description

Synthesis Analysis

This compound is recognized for its versatility as a starting material in the synthesis of nitrogenous heterocycles, including benzimidazoles, benzotriazoles, and quinoxalinones, via polymer-supported o-phenylendiamines. The method involves immobilization on Rink resin, followed by chlorine substitution, nitro group reduction, and cyclization, showcasing its reactivity and utility in constructing complex molecules (Křupková et al., 2013) .

Molecular Structure Analysis

The molecular structure of 2-Chloro-4-fluoro-5-nitrobenzoic acid and its derivatives has been extensively studied through X-ray diffraction techniques, revealing insights into its crystallography and molecular interactions. These studies emphasize the role of halogen bonds in the stabilization of its molecular structure and highlight its solid-state versatility (Oruganti et al., 2017).

Chemical Reactions and Properties

The chemical reactivity of 2-Chloro-4-fluoro-5-nitrobenzoic acid extends to its participation in various reactions, forming complexes and co-crystals with other compounds. Its ability to form hydrogen bonds with pyrazine, leading to different structural motifs, underscores its chemical versatility and potential for creating diverse molecular architectures (Ishida et al., 2001).

Physical Properties Analysis

The polymorphic behavior of 2-Chloro-4-nitrobenzoic acid, a closely related compound, has been reinvestigated to understand its solid-state properties. Studies involving infrared spectra, differential scanning calorimetry, and thermomicroscopy, alongside X-ray powder patterns, have provided valuable information on its physical characteristics and stability under various conditions (Barsky et al., 2008).

Chemical Properties Analysis

In-depth analyses of its chemical properties, facilitated by high-performance liquid chromatography and sensitive detection techniques, have demonstrated the compound's utility in the derivatization and detection of amino acids. This highlights its role in biochemical research and analytical chemistry, showcasing its broader applicability beyond synthesis (Watanabe & Imai, 1981).

Scientific Research Applications

• Synthesis of Heterocyclic Scaffolds : It serves as a multireactive building block for heterocyclic oriented synthesis, leading to condensed nitrogenous cycles like benzimidazoles, benzotriazoles, quinoxalinones, and others. This method is useful for drug discovery (Křupková et al., 2013) .
• Synthesis of Benzamide Derivatives : 2-Chloro-4-fluoro-5-nitrobenzoic acid is used in the synthesis of 4-amino-2-fluoro-N-methyl-benzamide, highlighting its utility in producing compounds with potential medicinal properties (Xu, Xu, & Zhu, 2013).
• Fluorimetric Determination of Amino Acids : It's used in fluorogenic reactions with secondary amino acids, superior in reactivity and fluorescence yield compared to analogous compounds. This application is significant in biochemical analysis and research (Imai & Watanabe, 1981).
• Phenotypic Screening in Drug Discovery : The compound aids in phenotypic screening processes in drug discovery, further underscoring its utility in medicinal chemistry (Miller & Mitchison, 2004) .
• Molecular Salts and Cocrystals Synthesis : 2-Chloro-4-nitrobenzoic acid, a related compound, is used in synthesizing molecular salts and cocrystals, illustrating its importance in crystal engineering and pharmaceutical formulation (Oruganti et al., 2017).

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