112898-33-6 | TRANS-2,5-DIFLUOROCINNAMIC ACID

CAS:112898-33-6 | TRANS-2,5-DIFLUOROCINNAMIC ACID,Description

Synthesis Analysis

The synthesis of trans-2,5-Difluorocinnamic acid and its analogs typically involves a one-pot reaction between homophthalic anhydrides and various aromatic aldehydes, followed by treatment with BBr3 or similar reagents. This method ensures the trans-configuration around the double bond, critical for the compound's desired properties and preventing isomerization (Miliovsky et al., 2015).

Molecular Structure Analysis

The molecular structure of trans-2,5-Difluorocinnamic acid and related compounds can be elucidated using spectroscopic methods, including gated decoupling 13C-NMR, which confirms the trans-configuration. The structure significantly influences the compound's reactivity and physical properties, as demonstrated in studies involving potential energy profile and vibrational analyses (Arjunan et al., 2016).

Chemical Reactions and Properties

Trans-2,5-Difluorocinnamic acid undergoes various chemical reactions, including [2+2] photodimerization, which can be influenced by external factors such as UV radiation and pressure. The reaction rates and mechanisms can vary significantly based on the structural configurations and environmental conditions, demonstrating the compound's versatile reactivity (Galica et al., 2016).

Physical Properties Analysis

The physical properties of trans-2,5-Difluorocinnamic acid, including its crystalline structure and phase behavior, can be affected by factors like pressure and temperature. These properties are crucial for understanding the compound's stability and reactivity under different conditions, as well as for designing new materials and chemical processes (Galica et al., 2018).

Chemical Properties Analysis

The chemical properties of trans-2,5-Difluorocinnamic acid, such as its antioxidative activity and potential for forming hybrid molecules with synergistic effects, are significant for various applications. These properties are often explored through SAR analysis and DFT quantum chemical computations, providing insights into the compound's mechanisms of action and potential uses (Miliovsky et al., 2015).

Scientific Research Applications

• Transformation in Peat Soils : Trans-4-hydroxycinnamic acid can transform during the fractionation of humic substances, playing a significant role in humus formation in acidic peat soils (Katase, 1985).
• Synthesis of trans-2-(Trifluoromethyl)cyclopropanes : These compounds can be synthesized using N-methyliminodiacetic acid boronate in Suzuki reactions with various coupling partners, showcasing moderate to excellent yields (Duncton & Singh, 2013).
• Antioxidant Activities : Polyhydroxylated trans-restricted 2-arylcinnamic acid analogues have been found to possess higher antioxidant activities than natural antioxidants, with a synergistic effect resulting in higher than expected activity (Miliovsky et al., 2015).
• Separation in Wine Production : Supercritical carbon dioxide can effectively separate three hydroxycinnamic acids from grape seeds and other natural substrates, potentially benefiting wine production (Murga et al., 2003).
• Mass Spectrometry Applications : Fluorine atoms decrease the stability of α-difluorocinnamic acids, allowing for identification of geometrical isomers through mass spectrometry (Parakhnenko et al., 1984).
• Conversion to Coumarins : Trans-o-fluorocinnamic acids can be converted to coumarins through thermal cyclisation, pyrolysis, and photolysis, yielding good coumarin derivatives (Heaney & Price, 1972).
• Self-Assembling Micelles : A photo-responsive system composed of 2-methoxycinnamic acid can self-assemble into viscoelastic worm-like micelles, with UV light irradiation causing structural isomerization (Du et al., 2015).
• Electrochemical Oxidation : Trans-3,4-dihydroxycinnamic acid at PbO2 electrodes shows potential for pollution abatement through efficient electrochemical oxidation methods (Amadelli et al., 2000).
• Reactivity under Pressure : The reactivity of difluorocinnamic acids under ambient and high pressures has been studied, revealing insights into their structural transformations (Galica et al., 2018).
• Pressure Influence on Photodimerization : The rate of photodimerization of 2,6-difluorocinnamic acid increases with pressure, demonstrating the influence of environmental conditions on chemical reactions (Galica et al., 2016).

Safety And Hazards

Trans-2,5-Difluorocinnamic acid may cause skin irritation, serious eye irritation, and respiratory irritation. It is recommended to avoid breathing its dust and to use it only outdoors or in a well-ventilated area. In case of contact with skin or eyes, it is advised to wash with plenty of water.

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