446-32-2 | 2-Amino-4-fluorobenzoic acid

CAS:446-32-2 | 2-Amino-4-fluorobenzoic acid,Description

Synthesis Analysis

The synthesis of 2-Amino-4-fluorobenzoic acid and related compounds involves several key strategies, including halogenation, nitration, and amination processes. For instance, Zhao Haoyu et al. (2010) describe the synthesis of 2-fluoro-6-iodobenzoic acid, a related compound, through carboxyl group protection, diazotization, iodosubstitution, and deprotection starting from 2-amino-6-fluorobenzoic acid, highlighting the versatile routes available for halogen-substituted benzoic acids (Zhao Haoyu, Zhang Qimeng, J. Tao, 2010).

Molecular Structure Analysis

The molecular structure of 2-Amino-4-fluorobenzoic acid and its derivatives can be elucidated using various spectroscopic and crystallographic techniques. Banerjee et al. (2022) conducted a detailed characterization of a co-crystal involving 4-fluorobenzoic acid, providing insights into the molecular interactions and stabilization mechanisms within the crystal structure through Hirshfeld surface analysis (B. Banerjee et al., 2022).

Chemical Reactions and Properties

2-Amino-4-fluorobenzoic acid participates in various chemical reactions, owing to the reactive amino group and the electron-withdrawing fluorine atom. These features enable it to undergo reactions such as amide formation, esterification, and coupling reactions, which are fundamental in synthesizing complex organic molecules. For example, the conversion of resin-bound 4-fluoro-3-nitrobenzoic acid to substituted 1,2-diaminobenzenes by Kilburn et al. (2000) demonstrates the compound's utility in solid-phase synthesis methodologies (J. Kilburn, J. Lau, Raymond C. F. Jones, 2000).

Scientific Research Applications

• Anticancer Applications : A lysyl amide prodrug of 2-(4-aminophenyl)-5-fluorobenzothiazole has been evaluated for its potential against breast and ovarian cancers, showing manageable toxic side effects (Bradshaw et al., 2002).
• Alzheimer's Disease Treatment : A fluorobenzoic acid derivative, specifically compound 3c, demonstrated potent inhibitory effects on enzymes relevant to Alzheimer's disease, suggesting its potential as a treatment agent (Czarnecka et al., 2017).
• Molecular Interactions and Crystallography : The co-crystal of 2-aminobenzothiazol with 4-fluorobenzoic acid showed a stable structure, highlighting its potential for molecular interaction studies (Banerjee et al., 2022).
• Solid-Phase Synthesis : A study presented a new strategy using resin-bound 4-fluoro-3-nitrobenzoic acid for synthesizing substituted 2-aminomethylbenzimidazoles (Kilburn et al., 2000).
• Chemical Synthesis Optimization : The optimal synthesis route for Methyl 2-amino-5-fluorobenzoate involved 3-fluorobenzoic acid, demonstrating a high yield of the target product (Yin Jian-zhong, 2010).
• Commercial Viability in Synthesis : The synthesis of 2-fluoro-6-iodobenzoic acid from 2-amino-6-fluorobenzoic acid resulted in a high purity product, suggesting commercial scalability (Zhao Haoyu et al., 2010).
• Fluorescence and Antioxidant Potential : The synthesis of 2-(2-carboxyphenylamino)-4-methylquinolines showed potential as efficient fluorophores and antioxidants (Aleksanyan & Hambardzumyan, 2013).
• Biochemical Analysis : A study involving 7-Fluoro-4-nitrobenzo-2-oxa-1,3-diazole enhanced high-performance liquid chromatography for sensitive detection of amino acids (Watanabe & Imai, 1981).
• Herbicidal Activity : 3-Chloro-4-fluorobenzoylthiourea demonstrated good herbicidal activity, indicating potential for pest control applications (Liu Chang-chun, 2006).
• Radiolabelling and Imaging : Rapid radiochemical synthesis of 18F-labelled peptides allowed for efficient PET imaging in tumor-bearing mice (Sutcliffe-Goulden et al., 2002).

Safety And Hazards

2-Amino-4-fluorobenzoic acid is considered hazardous by the 2012 OSHA Hazard Communication Standard (29 CFR 1910.1200). It causes skin irritation, serious eye irritation, and may cause respiratory irritation . Safety measures include washing off immediately with soap and plenty of water while removing all contaminated clothes and shoes, and getting medical attention .

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