175968-39-5 | 2,3-Difluoro-4-hydroxybenzoic acid

CAS:175968-39-5 | 2,3-Difluoro-4-hydroxybenzoic acid,Description

Synthesis Analysis

The synthesis of fluorinated benzoic acids, including 2,3-difluoro-4-hydroxybenzoic acid, often involves multi-step chemical processes that include nitration, esterification, reduction, diazotization, and hydrolysis. A practical approach has been demonstrated for the synthesis of closely related compounds, such as 3-chloro-2,4-difluoro-5-hydroxybenzoic acid, from 2,4-difluoro-3-chlorobenzoic acid with a notable overall yield of 70% (Zhang et al., 2020).

Molecular Structure Analysis

The molecular structure of 2,3-difluoro-4-hydroxybenzoic acid has been characterized using experimental techniques like FT-IR, FT-Raman, UV spectroscopy, and quantum chemical calculations. These studies provide insights into the molecule's conformation, vibrational and electronic transitions, and structural properties in the ground state. The optimized structure and vibrational wavenumbers offer a comparison with experimental results, facilitating a deeper understanding of the molecule's behavior at the molecular level (Karabacak et al., 2011).

Chemical Reactions and Properties

2,3-Difluoro-4-hydroxybenzoic acid participates in various chemical reactions, reflecting its versatile chemical properties. For instance, the fluorine atoms significantly influence its reactivity, making it a substrate for nucleophilic substitutions and other reactions relevant to synthetic chemistry. Studies on related fluorinated compounds provide evidence of their ability to undergo regiospecific hydroxylation and oxygenolytic dehalogenation mechanisms, hinting at the complex reaction pathways possible with fluorinated benzoic acids (van der Bolt et al., 1997).

Scientific Research Applications

• Synthesis of Antimicrobial Drugs : A practical synthesis method for 3-chloro-2,4-difluoro-5-hydroxybenzoic acid, closely related to 2,3-Difluoro-4-hydroxybenzoic acid, has been developed. This compound serves as a key intermediate in preparing antimicrobial 3-quinolinecarboxylic acid drugs (Zhang et al., 2020).
• Biosynthesis of Value-added Bioproducts : 4-Hydroxybenzoic acid, similar to 2,3-Difluoro-4-hydroxybenzoic acid, has emerged as a promising intermediate for producing various bioproducts with applications in food, cosmetics, pharmacy, and fungicides. Advanced biosynthetic techniques and synthetic biology approaches have been employed for this purpose (Wang et al., 2018) .
• Corrosion Inhibition : 3-Hydroxybenzoic acid, structurally similar to 2,3-Difluoro-4-hydroxybenzoic acid, has been studied for its potential use as a corrosion inhibitor for AISI 316L stainless steel in environmentally-friendly pickling solutions (Narváez et al., 2005) .
• Study of Molecular Structures : Research on the structures of 3-hydroxybenzoic acid and 4-hydroxybenzoic acid using electron diffraction and theoretical calculations provides insights that could be relevant for understanding the properties of 2,3-Difluoro-4-hydroxybenzoic acid (Aarset et al., 2008).
• Regiospecificity in Enzymatic Reactions : A study on the hydroxylation of various hydroxybenzoates, including tetrafluoro-4-hydroxybenzoate, by p-hydroxybenzoate hydroxylase, provides insights into the enzymatic reactions involving fluorinated benzoates (van der Bolt et al., 1997).
• Enzymatic Transformations in Microorganisms : Research on 3-Hydroxybenzoate 4-hydroxylase from Pseudomonas testosteroni highlights the enzymatic transformations of hydroxybenzoates, which may be applicable to 2,3-Difluoro-4-hydroxybenzoic acid (Michalover et al., 1973).

Safety And Hazards

The compound is classified as Acute Tox. 3 Oral, indicating that it is acutely toxic when ingested. It is also classified as a non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects.

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