153254-09-2 | 2,4-Bis(trifluoromethyl)phenylboronic acid

CAS:153254-09-2 | 2,4-Bis(trifluoromethyl)phenylboronic acid,Description

2,4-Bis(trifluoromethyl)phenylboronic acid is a boronic acid derivative characterized by the presence of two trifluoromethyl groups at the ortho and para positions on the phenyl ring. It has been identified as a highly effective catalyst in dehydrative amidation reactions between carboxylic acids and amines, which is crucial for α-dipeptide synthesis. The ortho-substituent plays a significant role in the catalytic process by preventing the coordination of amines to the boron atom, thus accelerating the amidation.

Synthesis Analysis

The synthesis of related bis(trifluoromethyl)phenyl derivatives has been reported through the reaction of RFLi with PnCl3, leading to a series of compounds with varying pnictogen centers. Although the exact synthesis of 2,4-bis(trifluoromethyl)phenylboronic acid is not detailed in the provided papers, similar synthetic routes involving halogen-lithium exchange followed by reaction with boron compounds could be inferred.

Molecular Structure Analysis

The molecular structure of 2,4-bis(trifluoromethyl)phenylboronic acid is not directly discussed in the provided papers. However, the structural analysis of related compounds, such as bis(2,4,6-tris(trifluoromethyl)phenyl) derivatives, has been confirmed through crystal structures and spectral data. These studies suggest that the trifluoromethyl substituents significantly influence the electronic properties of the molecule.

Chemical Reactions Analysis

2,4-Bis(trifluoromethyl)phenylboronic acid is primarily recognized for its catalytic activity in facilitating the formation of amide bonds. The ortho-substituent's role in preventing amine coordination to the boron atom is a key factor in its effectiveness as a catalyst. Additionally, the bis(trifluoromethyl)phenyl moiety has been utilized in other contexts, such as protective groups for diols, indicating its versatility in organic synthesis.

Physical and Chemical Properties Analysis

The physical and chemical properties of 2,4-bis(trifluoromethyl)phenylboronic acid are not explicitly described in the provided papers. However, the presence of trifluoromethyl groups is known to confer high stability and electron-withdrawing characteristics to the molecule, which can be inferred to affect its reactivity and physical properties. The related bis(trifluoromethyl)phenyl derivatives exhibit properties such as solubility in organic solvents and stability under various conditions.

Scientific Research Applications

Catalytic Applications

2,4-Bis(trifluoromethyl)phenylboronic acid has been found to be an effective catalyst in various chemical reactions. For instance, it catalyzes the dehydrative amidation between carboxylic acids and amines, playing a crucial role in accelerating amidation and facilitating α-dipeptide synthesis (Wang, Lu, & Ishihara, 2018). Moreover, it has been used as a catalyst in [4 + 3] cycloaddition reactions, enabling the preparation of cyclohepta[b]benzofurans and cyclohepta[b]indoles (Cao, Bian, & Zheng, 2015).

Material Synthesis

This compound plays a role in the synthesis of novel materials. For example, it has been used in the synthesis of star-shaped imide compounds containing electron-donating or electron-withdrawing side groups (Jeon & Yoon, 2012). Additionally, 2,4-bis(trifluoromethyl)phenylboronic esters, derived from this acid, have been applied as protective groups for diols in various organic transformations, illustrating its versatility in synthetic chemistry (Shimada et al., 2019).

Supramolecular Chemistry

In the field of supramolecular chemistry, 2,4-bis(trifluoromethyl)phenylboronic acid has been involved in the formation of rotaxanes through multicomponent self-assembly processes (Christinat, Scopelliti, & Severin, 2008). These rotaxanes have been characterized by X-ray crystallography, highlighting the compound's utility in creating complex molecular architectures.

Analytical Chemistry

In analytical chemistry, derivatives of this compound, such as 3,5-bis(trifluoromethyl)phenylboronic acid, have been utilized in gas chromatography as derivatizing reagents for halides, demonstrating its application in enhancing analytical methods (Yazdi & Stephen, 1992).

Tribology

In tribology, a study focused on a novel long-chain alkyl phenylboronic acid ester containing a heterocyclic compound derived from 2,4-bis(trifluoromethyl)phenylboronic acid. This ester showed outstanding hydrolytic stability and promising tribological properties, suggesting potential applications in lubrication and wear protection (Li et al., 2014).

Safety And Hazards

2,4-Bis(trifluoromethyl)phenylboronic acid is considered hazardous. It can cause skin irritation and serious eye irritation. In case of contact with skin or eyes, it’s recommended to wash off immediately with soap and plenty of water. If symptoms persist, seek medical attention.

More Information