157665-52-6 | TERT-BUTYL 3-FLUORO-4-NITROBENZOATE

CAS:157665-52-6 | TERT-BUTYL 3-FLUORO-4-NITROBENZOATE,Description

Synthesis Analysis

The synthesis of tert-butyl compounds often involves the use of tert-butyl groups as protective groups due to their steric bulk and ease of removal. For example, the synthesis of 2,4-Dimethoxy-1,3,5-benzenetriyltris(N-tert-butyl nitroxide) involves lithiation followed by reaction with 2-methyl-2-nitrosopropane and oxidation with Ag2O. Similarly, tert-butyl nitrite is used as a nitrosation reagent and an oxidant in the synthesis of 2-aminobenzophenones. These methods could potentially be adapted for the synthesis of tert-butyl 3-fluoro-4-nitrobenzoate by choosing appropriate starting materials and reaction conditions.

Molecular Structure Analysis

The molecular structure of tert-butyl compounds can be complex, as seen in the X-ray analysis of the triradical compound with large dihedral angles between the N-O bonds and the benzene ring plane. The tert-butyl group's steric bulk can influence the overall molecular conformation and reactivity.

Chemical Reactions Analysis

Tert-butyl groups are often involved in various chemical reactions. For instance, tert-butyl nitrite mediated synthesis involves multiple sp2 C-H bond functionalizations. The reactivity of the tert-butyl group in tert-butyl 3-fluoro-4-nitrobenzoate would likely be influenced by the electron-withdrawing effects of the nitro and fluoro substituents, which could affect its participation in chemical reactions.

Physical and Chemical Properties Analysis

The physical and chemical properties of tert-butyl compounds can vary widely. For example, poly(arylene ether ketone)s containing pendant tertiary butyl groups exhibit specific thermal and mechanical properties. The presence of tert-butyl groups can also affect the solubility and stability of compounds, as seen in the synthesis of aromatic polyimides. The tert-butyl group in tert-butyl 3-fluoro-4-nitrobenzoate would contribute to its physical properties, such as melting point and solubility, and its chemical properties, such as reactivity and stability.

Relevant Case Studies

While there are no direct case studies on tert-butyl 3-fluoro-4-nitrobenzoate, the papers provide examples of tert-butyl compounds used in various applications. For instance, tert-butyl nitrite is used as a synthon in the synthesis of complex heterocycles, and the photolysis of o-nitro-tert-butylbenzenes leads to specific photoproducts. These studies highlight the versatility of tert-butyl compounds in synthetic chemistry, which could be relevant for the application of tert-butyl 3-fluoro-4-nitrobenzoate in research and industry.

Scientific Research Applications

Chemical Synthesis and Molecular Structure Analysis

Tert-butyl 3-fluoro-4-nitrobenzoate has been explored in various chemical synthesis processes. For instance, its interaction with tert-butylamine and subsequent oxidation has been used to produce functionalized perfluorinated phenyl tert-butyl nitroxides. These compounds have been analyzed for their molecular and crystal structures using single crystal X-ray diffraction and confirmed by ESR data (Tretyakov et al., 2019). Additionally, tert-butyl 3-fluoro-4-nitrobenzoate derivatives have been synthesized and characterized using various spectroscopic techniques, contributing valuable insights into structural and conformational properties of these compounds (Gholivand et al., 2009).

Radiochemistry and Tumor Hypoxia Detection

In the field of radiochemistry, tert-butyl 3-fluoro-4-nitrobenzoate derivatives have been synthesized for potential applications in detecting tumor hypoxia. The synthesis involved coupling nitroimidazole with silyldinaphtyl or silylphenyldi-tert-butyl groups, leading to the production of compounds suitable for in vivo assessments (Joyard et al., 2013).

Supramolecular Chemistry and Self-Assembly

In supramolecular chemistry, tert-butyl 3-fluoro-4-nitrobenzoate has been used to create nanoscale particles capable of recognizing metal cations and dicarboxylic acids. These particles can form cascade or commutative three-component supramolecular systems, offering significant potential for the development of new materials (Yushkova et al., 2012).

Solid-Phase Synthesis

In the domain of solid-phase synthesis, tert-butyl 3-fluoro-4-nitrobenzoate has been utilized in the production of various derivatives. For example, its reaction with carbon nucleophiles has led to the synthesis of substituted 1-hydroxy-6-indolecarboxylic acids and benzo[c]isoxazoles, demonstrating the versatility of this compound in organic synthesis (Stephensen & Zaragoza, 1999).

Biological Evaluation

Tert-butyl 3-fluoro-4-nitrobenzoate derivatives have also been evaluated for their biological activities. For instance, a specific derivative was synthesized and screened for its in vitro antibacterial and anthelmintic activity, revealing moderate anthelmintic activity (Sanjeevarayappa et al., 2015).

Electrochemical Applications

The electrochemical properties of tert-butyl 3-fluoro-4-nitrobenzoate derivatives have been studied, particularly focusing on the nitrobenzoyl group's behavior as a protecting group for hydroxyl functionalities. This research has contributed to understanding the electrochemical behavior of various nitrobenzoate isomers (Jorge & Stradiotto, 1996).

Safety And Hazards

While the specific safety and hazards information for Tert-butyl 3-fluoro-4-nitrobenzoate is not available, general safety measures for handling similar compounds include avoiding ingestion and inhalation, ensuring adequate ventilation, keeping away from open flames, hot surfaces, and sources of ignition, and using only non-sparking tools. It’s also recommended to avoid dust formation and contact with skin and eyes.

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