1582-24-7 | 2,3,4,5,6-PENTAFLUOROBENZENEBORONIC ACID

CAS:1582-24-7 | 2,3,4,5,6-PENTAFLUOROBENZENEBORONIC ACID,Description

Synthesis Analysis

The synthesis of 2,3,4,5,6-Pentafluorobenzeneboronic acid derivatives and related compounds has been explored through various methods. A common approach involves the functionalization of pentafluorobenzene or its derivatives, utilizing boronic acid chemistry for the introduction of the boron-containing group. For example, the preparation of 2,3,4,5,6-Pentafluorobenzoic Acid from pentachlorobenzonitrile through fluorine exchange and subsequent hydrolysis demonstrates a related methodology in the fluorination and functionalization of aromatic compounds (Hui, 2007).

Molecular Structure Analysis

Investigations into the molecular structure and vibrational analysis of 2,3,4,5,6-pentafluorobenzoic acid, a close relative of the boronic acid derivative, have provided insights into the effects of fluorination on the aromatic system. DFT and HF methods have been applied to study the equilibrium geometry, vibrational wavenumbers, and potential for intermolecular hydrogen bonding, offering a glimpse into the structural characteristics that might also pertain to the boronic acid derivative (Subhapriya et al., 2015).

Chemical Reactions and Properties

The chemical reactivity of pentafluorophenyl compounds, including boronic acid derivatives, encompasses a range of reactions. These compounds participate in nucleophilic aromatic substitutions, offering pathways to introduce various functional groups. The synthesis and reactivity of low-coordinate iron(II) fluoride complexes with fluorocarbons, including pentafluorobenzene, highlight the potential of fluorinated aromatics in catalytic reactions, such as hydrodefluorination, which could be relevant for derivatives of 2,3,4,5,6-pentafluorobenzeneboronic acid (Vela et al., 2005).

Scientific Research Applications

• Polymer Chemistry : 2,3,4,5,6-Pentafluorobenzeneboronic acid derivatives are utilized in polymer chemistry for postpolymerization modifications, demonstrating its versatility as a precursor for various modifications with click-like efficiencies (Noy et al., 2019) .
• Chemical Reactions and Synthesis : Research shows the compound's reactivity under different conditions, providing valuable insights into the synthesis of various fluorinated compounds and their derivatives. This includes reactions with nitric acid and the formation of biphenyl and related compounds (Birchall et al., 1973).
• Synthesis of Natural Products : 2,3,4,5,6-Pentafluorobenzeneboronic acid derivatives have been used to facilitate difficult macrocyclizations in the synthesis of natural products like longithorone C (Zakarian et al., 2008).
• Molecular Structure Analysis : Studies have investigated the molecular structure and vibrational analysis of related compounds, offering insights into the intermolecular hydrogen bonding in derivatives of 2,3,4,5,6-Pentafluorobenzeneboronic acid (Subhapriya et al., 2015).
• Analytical Applications : Derivatives of 2,3,4,5,6-Pentafluorobenzeneboronic acid have been used in developing derivatizing agents for identifying polar ozonation drinking water disinfection by-products. These agents help in the extraction and analysis of such by-products (Vincenti et al., 2005).
• Fluorinated Polymers : It's an intermediate in the synthesis of novel fluorinated poly(ether nitrile)s, which are used in various applications due to their excellent solubility, thermal stability, and film-forming properties (Kimura et al., 2001).
• Solvation Structure in Supercritical Fluids : Studies involving 2,3,4,5,6-Pentafluorotoluene, a closely related compound, provide insights into solvation structures in supercritical carbon dioxide, which is significant for understanding fluid dynamics in these conditions (Kanakubo et al., 2002).
• Electrochemical Reduction : 2,3,4,5,6-Pentafluorobenzoic acid, a related compound, has been studied for its electrochemical reduction properties, providing insights into product-selective reductions, important for synthetic applications (Sato et al., 1992).

Safety And Hazards

2,3,4,5,6-Pentafluorobenzeneboronic acid causes skin irritation, serious eye irritation, and may cause respiratory irritation. It is recommended to avoid breathing dust/fume/gas/mist/vapors/spray, and to wear protective gloves/clothing/eye protection/face protection. In case of contact with eyes, rinse cautiously with water for several minutes.

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