110931-77-6 | 3-(2',4'-DIFLUOROBENZOYL)PROPIONIC ACID

CAS:110931-77-6 | 3-(2',4'-DIFLUOROBENZOYL)PROPIONIC ACID,Description

Synthesis Analysis

The synthesis of compounds related to 4-(2,4-Difluorophenyl)-4-oxobutanoic acid often involves ring-opening reactions of itaconic anhydride with aminoacetophenones, characterized by various spectroscopic methods including FT-IR, NMR, and X-ray diffraction (Nayak et al., 2014). Additionally, copper-catalyzed cross-coupling reactions have been employed for the synthesis of novel surfactants related to this compound, showcasing innovative approaches to its production (Chen et al., 2013).

Molecular Structure Analysis

The molecular structure of derivatives of 4-(2,4-Difluorophenyl)-4-oxobutanoic acid has been elucidated through single crystal X-ray diffraction studies, revealing detailed geometrical parameters and crystal packing influenced by hydrogen bonding and other non-covalent interactions (Ashfaq et al., 2021). DFT calculations complement these findings by providing insights into the stability, charge distribution, and reactive sites of the molecules.

Chemical Reactions and Properties

Chemical reactions involving 4-(2,4-Difluorophenyl)-4-oxobutanoic acid derivatives include cyclisation reactions, where the structure of the resulting compounds depends significantly on the substrate used, showcasing the compound's versatility in synthetic chemistry (Amalʼchieva et al., 2022) . The compound and its derivatives exhibit various bioactive properties, including inhibition of glycolic acid oxidase, highlighting its potential pharmacological relevance (Williams et al., 1983).

Physical Properties Analysis

Studies have shown that 4-(2,4-Difluorophenyl)-4-oxobutanoic acid derivatives can form premicellar aggregates, indicating unique surfactant properties. These findings are supported by dynamic light scattering and atomic force microscopy analyses (Chen et al., 2013).

Chemical Properties Analysis

The chemical properties of 4-(2,4-Difluorophenyl)-4-oxobutanoic acid derivatives have been extensively studied through spectroscopic, DFT, MD, and docking studies. These studies reveal the compound's nonlinear optical properties, reactive centers, and potential for biological activity inhibition, underscoring its multifaceted nature and applicability in various scientific domains (Mary et al., 2017).

Scientific Research Applications

1. Synthesis and Antioxidant Activity Evaluation

• Methods of Application: The compounds were synthesized by reaction of 4-(4-X-phenylsulfonyl)benzoic acids hydrazides with 2,4-difluorophenyl isothiocyanate. These were then treated with sodium hydroxide to obtain 1,2,4-triazole-3-thione derivatives. The reaction of these derivatives with α-halogenated ketones, in basic media, afforded new S-alkylated derivatives.
• Results or Outcomes: The antioxidant activity of all compounds was screened. Hydrazinecarbothioamides showed excellent antioxidant activity and 1,2,4-triazole-3-thiones showed good antioxidant activity using the DPPH method.

2. Suzuki-Miyaura Cross-Coupling Reactions

• Methods of Application: The specific methods of application in this case would depend on the exact nature of the Suzuki-Miyaura cross-coupling reaction being performed. Generally, this reaction involves the coupling of an aryl or vinyl boronic acid with an aryl or vinyl halide or triflate in the presence of a palladium catalyst and a base.
• Results or Outcomes: The outcomes of these reactions are biaryl compounds, which have wide applications in pharmaceuticals, agrochemicals, and functional materials.

3. Crystallography

• Application Summary: The molecular structure of 2,4-Difluorophenylboronic acid, a compound related to 4-(2,4-Difluorophenyl)-4-oxobutanoic acid, was studied using crystallography.
• Methods of Application: The compound was crystallized and its structure was analyzed using X-ray diffraction.
• Results or Outcomes: The molecular structure of the compound was found to be essentially planar, indicating electronic delocalization between the dihydroxy-boryl group and the aromatic ring.

4. Phosphorescent Sensor for Biologically Mobile Zinc and Blue Green Phosphorescent OLEDs

• Application Summary: 2,4-Difluorophenylboronic acid is used in the development of phosphorescent sensors for biologically mobile zinc and blue-green phosphorescent organic light-emitting diodes (OLEDs).
• Methods of Application: The specific methods of application would depend on the exact nature of the sensor or OLED being developed.
• Results or Outcomes: The outcomes of these applications are advanced sensors and OLEDs.

5. End Group Capping

• Application Summary: 2,4-Difluorophenylboronic acid is used in end group capping, a process used in polymer chemistry to modify the properties of polymers.
• Methods of Application: The specific methods of application would depend on the exact nature of the polymer and the desired properties.
• Results or Outcomes: The outcomes of these applications are modified polymers with desired properties.

6. Synthesis of 2-(2,4-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

• Application Summary: 2,4-Difluorophenylboronic acid is used in the synthesis of 2-(2,4-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, a compound that could have various applications in organic synthesis.
• Methods of Application: The specific methods of application would depend on the exact nature of the synthesis.
• Results or Outcomes: The outcome of this application is the synthesis of 2-(2,4-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Safety And Hazards

The safety and hazards associated with 4-(2,4-Difluorophenyl)-4-oxobutanoic acid are not known. However, related compounds such as 3,5-Difluorophenol are known to be harmful if swallowed, in contact with skin, or if inhaled⁷.

Future Directions

There is no specific information available on the future directions of research or applications for 4-(2,4-Difluorophenyl)-4-oxobutanoic acid. However, the study and development of fluorinated compounds is an active area of research due to their potential applications in various fields, including medicine and materials science⁴.

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