14027-75-9 | 3-FLUORO-5-NITROBENZOIC ACID

CAS:14027-75-9 | 3-FLUORO-5-NITROBENZOIC ACID,Description

3-Fluoro-5-nitrobenzoic acid is a multifunctional compound used as a building block in organic chemistry, particularly in the synthesis of various heterocyclic compounds. It is recognized for its role in creating nitrogenous cycles, which are significant in drug discovery and development.

Synthesis Analysis

• 3-Fluoro-5-nitrobenzoic acid can be synthesized using 4-chloro-2-fluoro-5-nitrobenzoic acid, a readily available compound. This synthesis can lead to various condensed nitrogenous cycles, including benzimidazoles, benzotriazoles, and quinoxalinones, among others (Křupková et al., 2013) .

Molecular Structure Analysis

• The molecule of a closely related compound, 4-(acetylamino)-3-hydroxy-5-nitrobenzoic acid, which is a designed inhibitor for the influenza virus neuraminidase protein, forms hydrogen-bonded dimers. The dihedral angles of its substituent groups provide insights into the structural configuration (Jedrzejas et al., 1995).

Chemical Reactions and Properties

• In reactions involving 3,5-dinitro- and 3-fluoro-5-nitrobenzofluorides, the mobility of the nitro group and fluorine atom is significant. These reactions, often involving phenols, are guided by the reactivity of arenes and can be entropy-controlled (Khalfina & Vlasov, 2002).

Physical Properties Analysis

• The crystal structure of 3-nitrobenzoic acid and its complexes, closely related to 3-fluoro-5-nitrobenzoic acid, demonstrates unique bonding features and physical properties that could be extrapolated to understand the properties of 3-fluoro-5-nitrobenzoic acid (D'angelo et al., 2008).

Chemical Properties Analysis

• Studies on compounds like 5-fluoroisoxazoles, synthesized via the reaction of nitrosonium with bromo-fluoro arylcyclopropanes, can provide insights into the chemical behavior and potential applications of 3-fluoro-5-nitrobenzoic acid (Bondarenko et al., 2019).

Scientific Research Applications

• Synthesis of Guanine-Mimetic Library : 3-Fluoro-5-nitrobenzoic acid has been used in the synthesis of a guanine-mimetic library. This demonstrates its utility in the creation of complex organic compounds that mimic biological molecules (Miller & Mitchison, 2004) .
• Building Block for Solid-Phase Synthesis : It serves as a multireactive building block in heterocyclic oriented synthesis, useful for creating various nitrogenous heterocycles, which are significant in drug discovery (Křupková et al., 2013) .
• Synthesis of β-Turn Peptidomimetics : The compound is used in the synthesis of β-turn peptidomimetics, playing a role in the development of peptide-based pharmaceuticals (Jiang & Burgess, 2002) .
• Fluorescent Labeling Reagent in Chromatography : 3-Fluoro-5-nitrobenzoic acid derivatives are used as fluorescent labeling reagents in chromatography for the detection of amino acids (Watanabe & Imai, 1981).
• Synthesis of Various Organic Compounds : It's involved in the solid-phase synthesis of N-hydroxyindoles, benzo[c]isoxazoles, and other complex organic compounds (Stephensen & Zaragoza, 1999).
• Use in Flow Chemistry : 3-Fluoro-5-nitrobenzoic acid and its derivatives are involved in flow chemistry processes, indicating their importance in the manufacturing of fine chemicals and pharmaceutical intermediates (Chen et al., 2020).
• Synthesis of Biaryl Ethers and Macrocycles : The compound is also a key reagent in the solid-phase synthesis of functionalized biaryl ethers and macrocycles, which are useful scaffolds in combinatorial chemistry (Wijkmans et al., 1997; Kiselyov et al., 1998; Kiselyov et al., 1999).

Safety And Hazards

3-Fluoro-5-nitrobenzoic acid can cause skin irritation and serious eye irritation. It may also cause respiratory irritation. It is recommended to avoid breathing its dust/fume/gas/mist/vapors/spray and to use it only outdoors or in a well-ventilated area.

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