448-19-1 | 5-Fluoro-2-nitroanisole

CAS:448-19-1 | 5-Fluoro-2-nitroanisole,Description

5-Fluoro-2-nitroanisole is a chemical compound that is part of the broader class of nitroanisoles, which are characterized by a nitro group (-NO2) and a methoxy group (-OCH3) attached to a benzene ring. The specific position of the fluoro and nitro substituents on the benzene ring can significantly influence the chemical and physical properties of the compound, as well as its reactivity in various chemical reactions.

Synthesis Analysis

The synthesis of fluoronitro alkanes, which are structurally related to 5-Fluoro-2-nitroanisole, has been achieved through a multi-step process involving the displacement of iodide from perfluoroalkanes with sodium nitrite followed by oxidative nitration. This method showcases the potential for synthesizing fluorinated nitro compounds, which could be adapted for the synthesis of 5-Fluoro-2-nitroanisole.

Molecular Structure Analysis

While the papers provided do not directly discuss the molecular structure of 5-Fluoro-2-nitroanisole, they do provide insights into the structures of related compounds. For instance, the Ni(II) complexes with 5-nitroorotate ligands demonstrate how nitro and other functional groups can coordinate with metal ions, which could be relevant for understanding the coordination chemistry of 5-Fluoro-2-nitroanisole.

Chemical Reactions Analysis

The photoreaction of 2-fluoro-4-nitroanisole with n-hexylamine, which is structurally similar to 5-Fluoro-2-nitroanisole, results in fluoride and methoxy substitution. This reaction proceeds through different triplet excited states, indicating that the position of the fluoro and nitro groups on the anisole ring can influence the reaction pathway and the nature of the excited states involved. Additionally, the photosubstitution of 2-fluoro-4-nitroanisole with various amines suggests that nitrophenyl ethers, which are related to 5-Fluoro-2-nitroanisole, could serve as useful photoprobes in biochemical applications.

Physical and Chemical Properties Analysis

The physical and chemical properties of 5-Fluoro-2-nitroanisole can be inferred from related compounds. For example, the complexes of copper(II), nickel(II), and cobalt(II) with fluoronitroanilines exhibit a range of coordination geometries and magnetic properties, which are influenced by the presence of the fluoro and nitro groups. Similarly, the synthesis and characterization of fluorinated benzimidazole-substituted nitronyl nitroxides provide insights into the acidity and redox properties of fluorinated nitro compounds, which could be relevant for understanding the behavior of 5-Fluoro-2-nitroanisole under different conditions.

Scientific Research Applications

Fluorinated Compounds in Cancer Research

Fluorinated compounds, such as 5-Fluorouracil (5-FU), have significant applications in cancer research and treatment. Although not directly mentioning 5-Fluoro-2-nitroanisole, studies on fluorinated pyrimidines, including 5-FU, highlight the broader context of fluorinated compounds in oncology. These compounds interfere with DNA synthesis, showcasing their potential in palliating advanced cancer, particularly in tumors of the breast and gastrointestinal tract (Heidelberger & Ansfield, 1963). Further research delves into the synthesis methods of 5-FU and its analogs, emphasizing the role of fluorinated intermediates in creating effective cancer therapeutics (Gmeiner, 2020).

Fluorinated Liquid Crystals

The impact of fluorinated compounds extends into materials science, particularly in the development of fluorinated liquid crystals. These materials exhibit modified melting points, mesophase morphology, and optical properties due to the incorporation of fluorine atoms. Fluorinated liquid crystals find applications in display technologies and other commercial uses, indicating the potential utility of 5-Fluoro-2-nitroanisole in synthesizing new liquid crystal materials (Hird, 2007).

Energetic Materials Research

In the field of high-energy materials, the study of nitro-containing compounds like 5-Fluoro-2-nitroanisole is crucial. These studies often focus on the crystal structure, thermolysis, and applications of nitro compounds in energetic materials, providing insights into their potential uses in propellants, explosives, and pyrotechnics (Singh & Felix, 2003).

Fluorescence Imaging and Diagnosis

The application of fluorinated compounds in fluorescence imaging and diagnosis, especially in neuro-oncological surgery, showcases the utility of these molecules in enhancing the visualization of tumors. While not directly related to 5-Fluoro-2-nitroanisole, the research on intraoperative fluorophores, such as 5-aminolevulinic acid (5-ALA) and others, underlines the importance of fluorinated molecules in medical imaging and cancer surgery (Acerbi et al., 2022).

Safety And Hazards

The safety data sheet for 5-Fluoro-2-nitroanisole provides information on its hazards, including that it causes skin irritation, serious eye irritation, and is suspected of causing genetic defects. It also provides precautionary statements, such as obtaining special instructions before use, washing hands thoroughly after handling, wearing protective gloves/clothing/eye protection/face protection, and storing locked up.

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