1072951-50-8 | 2-Hydroxy-4-(trifluoromethyl)phenylboronic acid

CAS:1072951-50-8 | 2-Hydroxy-4-(trifluoromethyl)phenylboronic acid,Description

Boronic acids are a class of compounds known for their unique reactivity and utility in organic synthesis. They are particularly recognized for their ability to form reversible covalent bonds with hydroxy groups, which can be exploited in various organic reactions. The compound "(2-Hydroxy-4-(trifluoromethyl)phenyl)boronic acid" is a derivative of phenylboronic acid with a trifluoromethyl group and a hydroxyl group on the phenyl ring. This structure suggests potential reactivity in catalysis and complexation reactions, similar to other boronic acids described in the literature.

Synthesis

Scientific Research Applications

1. Catalytic Applications

(2-Hydroxy-4-(trifluoromethyl)phenyl)boronic acid has been identified as an effective catalyst for dehydrative amidation between carboxylic acids and amines. This catalysis is crucial for alpha-dipeptide synthesis, showcasing its relevance in peptide chemistry (Wang, Lu, & Ishihara, 2018).

2. Hydroboration Reactions

Boronic acids, including variants like (2-Hydroxy-4-(trifluoromethyl)phenyl)boronic acid, play a role in hydroboration reactions. For instance, (Yin, Soltani, Melen, & Oestreich, 2017) discusses how these compounds are used in metal-free hydroboration of imines.

3. Functionalization and Modification of Carbon Nanotubes

Phenyl boronic acids, including this specific variant, have been used to modify carbon nanotubes, affecting their optical properties, as explored in the study by (Mu et al., 2012). This functionalization technique is vital for applications in nanotechnology and materials science.

4. Protective Groups in Organic Synthesis

The compound has applications in organic synthesis, particularly as a protective group for diols. This is exemplified by the work of (Shimada et al., 2018), where it was used in the synthesis of a natural product with anti-angiogenic activities.

5. Multifunctional Compound Synthesis

Research by (Zhang et al., 2017) delves into the synthesis of compounds where boronic acid is combined with aminophosphonic acid groups, highlighting its role as a building block in the creation of multifunctional compounds.

6. Boronic Acid Catalysis

Boronic acids are increasingly recognized for their role as catalysts in various organic reactions, as discussed in (Hall, 2019). They are used for activating hydroxy functional groups, leading to transformations into useful products.

7. Holographic Sensors

Boronic acids, including (2-Hydroxy-4-(trifluoromethyl)phenyl)boronic acid, have been incorporated into holographic sensors for detecting molecules like L-lactate. This application is explored in (Sartain, Yang, & Lowe, 2008).

8. Carbohydrate Recognition

Phenyl boronic acids, including this variant, are used in the recognition of carbohydrates. A study by (Dowlut & Hall, 2006) emphasizes their ability to bind carbohydrates under physiologically relevant conditions.

9. Organocatalytic Beckmann Rearrangement

The compound has been used in the Beckmann rearrangement, facilitating the transformation of oximes into functionalized amide products. This application is detailed by (Mo, Morgan, Ang, & Hall, 2018).

10. Lewis Acid Catalysis

Boronic acids, including (2-Hydroxy-4-(trifluoromethyl)phenyl)boronic acid, can act as Lewis acids in various reactions. For instance, (Erker, 2005) discusses its use in catalytic hydrometallation reactions and alkylations.

11. Photoluminescence Modulation

(Mu et al., 2012) also demonstrates how this compound can be used to modulate the photoluminescence of single-walled carbon nanotubes, a significant application in materials science and sensor technology.

12. Analytical Chemistry Applications

The compound's role in analytical chemistry is also significant. For instance, (Sengupta & Balasubramanian, 1991) discusses its use in the study of boron complexes in extraction-photometry.

13. Structural Analysis with NMR Spectroscopy

(Valenzuela et al., 2022) highlights the use of 11B NMR spectroscopy for analyzing the acidity and reactivity of phenyl boronic acid-diol condensations, an important aspect in understanding the chemistry of boronic acids.

Safety And Hazards

This compound is considered hazardous. It may cause skin irritation, serious eye irritation, and may cause respiratory irritation. Therefore, it is recommended to avoid dust formation, avoid breathing mist, gas or vapours, avoid contacting with skin and eye, and use personal protective equipment.

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