312936-89-3 | 2-METHOXY-4-(TRIFLUOROMETHYL)-PHENYLBORONIC ACID

CAS:312936-89-3 | 2-METHOXY-4-(TRIFLUOROMETHYL)-PHENYLBORONIC ACID,Description

(2-Methoxy-4-(trifluoromethyl)phenyl)boronic acid is a boronic acid derivative characterized by the presence of a methoxy group and a trifluoromethyl group on the phenyl ring. Boronic acids are known for their versatility in organic synthesis and their ability to form reversible covalent bonds with diols, which is useful in various chemical reactions and applications, including sensing and material sciences.

Synthesis Analysis

While the provided papers do not directly describe the synthesis of (2-Methoxy-4-(trifluoromethyl)phenyl)boronic acid, they do provide insights into the synthesis of related boronic acid compounds. For instance, the synthesis of boronic acids often involves the use of special boron Lewis acids, such as tris(pentafluorophenyl)borane, which can catalyze various reactions including hydrometallation and alkylation. The ortho-substituent on phenylboronic acids, similar to the one , plays a crucial role in the reactivity and stability of the boronic acid during catalytic processes.

Molecular Structure Analysis

The molecular structure of boronic acids is influenced by their substituents. For example, the crystal structure of difluoro[2-(4-methoxyphenyl)-3-oxo-3-phenylpropanalato]boron(III) shows that boron is tetrahedrally coordinated to two oxygen atoms and two fluorine atoms. Similarly, (2-Methoxy-4-(trifluoromethyl)phenyl)boronic acid would have a tetrahedral geometry around the boron atom, with the methoxy and trifluoromethyl groups influencing its electronic properties and reactivity.

Chemical Reactions Analysis

Boronic acids are known to participate in various chemical reactions. For example, they can be used as catalysts in dehydrative condensation reactions between carboxylic acids and amines. They are also involved in the hydrosilylation of amides, demonstrating functional group tolerance and the ability to proceed under mild conditions. The presence of electron-withdrawing groups, such as trifluoromethyl, can affect the reactivity and stability of the boronic esters formed during these reactions.

Physical and Chemical Properties Analysis

The physical and chemical properties of boronic acids are greatly influenced by their substituents. The presence of a methoxy group can affect the hydrogen bonding network and the solubility of the compound. The trifluoromethyl group, being highly electronegative, can increase the acidity of the boronic acid and enhance its reactivity in Suzuki-Miyaura coupling reactions, as seen with related polyfluorophenylboronic acids. Additionally, the binding affinity of boronic acids to diols and sugars can be modulated by the electronic nature of the substituents, which is important for applications in sensing and recognition.

Scientific Research Applications

(1) Catalyst in Dehydrative Amidation (2-Methoxy-4-(trifluoromethyl)phenyl)boronic acid has been reported as a highly effective catalyst for dehydrative amidation between carboxylic acids and amines, particularly in the synthesis of α-dipeptides. The ortho-substituent of boronic acid is crucial in preventing the coordination of amines to the boron atom of the active species, thereby accelerating the amidation process (Wang, Lu, & Ishihara, 2018).

(2) Structural Studies and Multifunctional Applications This boronic acid and its derivatives have been utilized in structural studies due to their multifunctional nature, allowing new opportunities for application in various fields such as medicine, agriculture, and industrial chemistry. For instance, (2-Methoxy-4-(trifluoromethyl)phenyl)boronic acid derivatives, featuring a combination of boronic acid with an aminophosphonic acid group, exhibit intriguing structural and functional properties (Zhang et al., 2017).

(3) Studies in Fluorescence Quenching This compound has been studied for its role in fluorescence quenching. Research involving two boronic acid derivatives, including (2-Methoxy-4-(trifluoromethyl)phenyl)boronic acid, has revealed insights into the conformational changes and interaction dynamics in various alcohol environments, contributing to the understanding of molecular fluorescence properties (Geethanjali et al., 2015).

(4) Direct Amide Formation Catalysts (2-Methoxy-4-(trifluoromethyl)phenyl)boronic acid and its derivatives have been shown to act as catalysts for direct amide formation between carboxylic acids and amines. These catalysts display varying reactivities based on the presence of electron-withdrawing or electron-donating groups, providing valuable insights into reaction optimization and catalyst design (Arnold et al., 2008).

(5) Sugar-Binding Interactions The binding interactions between (2-Methoxy-4-(trifluoromethyl)phenyl)boronic acid and various sugars have been investigated. These studies highlight the role of structural changes in sugars, particularly the importance of furanose forms, in the binding affinity and the formation of boronic esters. This research is pivotal for understanding the molecular basis of carbohydrate recognition and sensor development (Bhavya et al., 2016).

Safety And Hazards

The compound has been assigned the GHS07 pictogram. The hazard statements associated with it are H302-H315-H319-H332-H335. Precautionary measures include avoiding contact with skin and eyes, avoiding formation of dust and aerosols, and using non-sparking tools.

Future Directions

The compound has been used in the synthesis of pyrazine derivatives as corticotropin-releasing factor-1 receptor antagonists. This suggests potential applications in the field of medicinal chemistry.

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