186590-04-5 | 4-FLUORO-3-HYDROXYBENZONITRILE 98

CAS:186590-04-5 | 4-FLUORO-3-HYDROXYBENZONITRILE 98,Description

Synthesis Analysis

The synthesis of 4-Fluoro-3-hydroxybenzonitrile and related compounds involves multiple steps, including fluorination, nitrification, diazotization, and reductive and oxidation reactions. A study by Min (2006) highlights a synthesis approach using ortho-toluidine, achieving a successful productivity of 48% and indicating the process's control and practical importance for developing new pesticides (Min, 2006).

Molecular Structure Analysis

Research on 4-(2'-fluoro-4'-cyanophenoxy)anisole, a derivative of 4-Fluoro-3-hydroxybenzonitrile, provides insights into the molecular structure through IR, NMR, and single crystal X-ray diffraction analysis. This study confirms the molecule's non-coplanarity and the presence of intra- and inter-molecule hydrogen bonding, highlighting the structural dynamics of such compounds (Wang Lie-ping, 2007).

Chemical Reactions and Properties

The chemical reactions involving 4-Fluoro-3-hydroxybenzonitrile are complex, involving halogen-exchange fluorination and the use of various catalysts and conditions to achieve desired derivatives. Suzuki and Kimura (1991) described a method for synthesizing 3,4-difluorobenzonitrile, a related compound, demonstrating the intricate reactions and conditions necessary for fluorination processes (Suzuki & Kimura, 1991).

Physical Properties Analysis

Studies on the synthesis and properties of compounds like 4-Fluoro-3-hydroxybenzonitrile often include an examination of their physical properties, such as liquid-crystal transition temperatures. Kelly and Schad (1984) reported on the transition temperatures of ester derivatives, indicating how fluorine substitution affects the nematic-isotropic transition temperatures (Kelly & Schad, 1984).

Chemical Properties Analysis

The chemical properties of 4-Fluoro-3-hydroxybenzonitrile derivatives can be influenced by the presence of fluorine, affecting their reactivity and stability. The study by Ribeiro da Silva et al. (2012) provides an energetic and structural examination of monofluorobenzonitriles, offering insights into the enthalpies of formation and vapor pressures, which are crucial for understanding the chemical behavior of these compounds (Ribeiro da Silva, Monte, Rocha, & Cimas, 2012).

Scientific Research Applications

Synthesis and Structural Applications

The synthesis of ester derivatives of 2-fluoro-4-hydroxy- and 3-fluoro-4-hydroxybenzonitriles, which incorporate aliphatic ring systems such as trans-1,4-disubstituted cyclohexane or 1,4-disubstituted bicyclo[2.2.2]octane rings, has been explored. These compounds exhibit higher nematic-isotropic transition temperatures compared to their unsubstituted counterparts, indicating their potential application in the development of materials with specific liquid-crystalline properties (Kelly & Schad, 1984).

Electronic and Structural Properties

An energetic and structural study on mono-fluorobenzonitriles, including 2-fluoro-, 3-fluoro-, and 4-fluorobenzonitrile, has been conducted. This research involved determining the standard molar enthalpies of formation, vaporization, and sublimation, along with vapor-pressure studies and theoretical calculations. These studies contribute to understanding the electronic effects induced by the fluorine atom in the benzonitrile structure, which can influence the design of materials and chemicals with desired electronic properties (Ribeiro da Silva et al., 2012).

Radiofluorination and Biomedical Applications

The development of radiofluorinated 4-fluorobenzonitrile oxide and N-hydroxy-4-fluorobenzimidoyl chloride for rapid reaction with alkenes and alkynes under mild conditions has been reported. This method is suitable for preparing low-molecular-weight radiopharmaceuticals and could facilitate the labeling of sensitive biopolymers, suggesting potential applications in the development of novel diagnostic and therapeutic agents (Zlatopolskiy et al., 2012).

Chemical Interactions and Molecular Dynamics

The conversion of 4-hydroxybenzonitrile to its anion has been studied through IR spectra and ab initio calculations, revealing significant spectral changes and structural adjustments. This research provides insights into the chemical interactions and molecular dynamics of such compounds, which could be relevant for understanding their behavior in various chemical environments (Binev, 2001).

Photodegradation and Environmental Impact

The photodegradation of bromoxynil, a compound structurally similar to 4-fluoro-3-hydroxybenzonitrile, in the presence of carbonates has been investigated. This research could provide valuable information on the environmental behavior and degradation pathways of similar compounds, aiding in the assessment of their environmental impact (Kochany, 1992).

Safety And Hazards

4-Fluoro-3-hydroxybenzonitrile is classified as acutely toxic if swallowed, harmful in contact with skin, and may cause respiratory irritation. It is recommended to avoid dust formation, inhalation, and contact with skin and eyes.

Future Directions

As an intermediate in chemical synthesis, the future directions for 4-Fluoro-3-hydroxybenzonitrile largely depend on the development of new synthetic routes and target molecules in the pharmaceutical and fine chemical industries.

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