61324-93-4 | 4-fluoro-3-nitroanisole

CAS:61324-93-4 | 4-fluoro-3-nitroanisole,Description

4-Fluoro-3-nitroanisole is a chemical compound that has garnered attention due to its potential applications in various fields, including the synthesis of dyes, pharmaceuticals, and insecticides. It is a derivative of aniline, where the aniline molecule is substituted with a fluoro group at the fourth position and a nitro group at the third position. This compound serves as an intermediate in the synthesis of more complex molecules and has been studied for its unique properties and reactivity.

Synthesis Analysis

The synthesis of related fluorinated compounds has been explored through various methods. For instance, fluoronitroalkenes have been used in a one-pot three-component route to create fluorinated nitroso acetals with high regioselectivity and stereoselectivity, indicating the potential for synthesizing complex molecules from simpler fluorinated precursors like 4-fluoro-3-nitroanisole. Additionally, the synthesis of 3-Fluoro-4-nitrophenol, a compound structurally similar to 4-fluoro-3-nitroanisole, has been achieved through a multi-step process starting from m-fluoroaniline, demonstrating the feasibility of synthesizing fluoric intermediates through diazotization, hydrolysis, nitration, and separation of isomers.

Molecular Structure Analysis

The molecular structure of compounds related to 4-fluoro-3-nitroanisole has been investigated using various techniques. For example, the molecular structures and conformations of 4-fluoroanisole and 3,4-difluoroanisole were studied by gas electron diffraction and quantum chemical methods, revealing that 4-fluoroanisole exists as a single conformer with the O–CH3 bond in the plane of the aromatic ring. This suggests that the molecular structure of 4-fluoro-3-nitroanisole could also exhibit specific conformational properties that influence its reactivity and physical properties.

Chemical Reactions Analysis

The reactivity of compounds similar to 4-fluoro-3-nitroanisole has been the subject of various studies. For instance, the photosubstitution reactions of 2-fluoro-4-nitroanisole with nucleophiles have been explored, indicating that these types of compounds can undergo regioselective substitution reactions under photochemical conditions. These findings are relevant to understanding the chemical behavior of 4-fluoro-3-nitroanisole under similar conditions.

Physical and Chemical Properties Analysis

The physical and chemical properties of compounds analogous to 4-fluoro-3-nitroanisole have been characterized in several studies. For example, 4-fluoro 4-nitrostilbene (FONS), a compound with a similar substitution pattern, was synthesized and its properties were extensively studied. The crystal structure, spectral properties, thermal behavior, and nonlinear optical properties were determined, providing insights into the potential properties of 4-fluoro-3-nitroanisole. Additionally, the formation of metal complexes with derivatives of fluoro-nitroaniline has been reported, which could suggest the ability of 4-fluoro-3-nitroanisole to form complexes with metals, influencing its physical and chemical properties.

Scientific Research Applications

Photoreaction Mechanisms

4-Fluoro-3-nitroanisole is explored for its photoreaction mechanisms. The photosubstitution of similar compounds, like 2-fluoro-4-nitroanisole, with various nucleophiles has been studied, suggesting their potential as biochemical photoprobes (Pleixats et al., 1989). These studies contribute to understanding how these compounds interact under light exposure, which is crucial for developing light-sensitive biochemical tools.

Synthesis Techniques

Research into the synthesis of closely related compounds, like 3-Fluoro-4-nitrophenol, provides insights into the chemical processes needed for producing 4-Fluoro-3-nitroanisole. Techniques such as methoxylation and demethylation are employed, offering a basis for similar synthesis processes (Zhang Zhi-de, 2011).

Industrial Applications

4-Fluoro-3-nitroaniline, a derivative of 4-Fluoro-3-nitroanisole, is significantly important in the U.S. as a novel dye intermediate. It also holds potential for use in pharmaceuticals and insecticides (Bil, 2007) . This highlights the industrial relevance of 4-Fluoro-3-nitroanisole and its derivatives in various sectors.

Environmental Impact

The environmental impact of nitroaromatic compounds, including 4-nitroanisole, is studied due to their use in agriculture and military applications. Their transformation under aerobic conditions and potential formation of more toxic compounds like azo dimers is of significant concern (Kadoya et al., 2018). Understanding the environmental behavior of these compounds is crucial for assessing their ecological impact.

Electrophilic Substitution Mechanisms

Studies on the electrophilic substitution reactions of similar compounds, such as 4-nitroanisole, provide insight into the reactivity and possible chemical transformations of 4-Fluoro-3-nitroanisole. These reactions are essential for the creation of various industrial and pharmaceutical compounds (Bloomfield et al., 1983).

Safety And Hazards

4-Fluoro-3-nitroanisole is harmful if swallowed and may cause skin and eye irritation. It may also cause respiratory irritation. Safety measures include avoiding breathing its dust/fume/gas/mist/vapors/spray, and using it only outdoors or in a well-ventilated area. In case of contact with skin or eyes, or if swallowed, medical attention should be sought.

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