69002-86-4

Usage

Uses

Used in Pharmaceutical Industry:
(2-(2,6-Dichloro-4-hydroxyanilino)-5-hydroxyphenyl)acetic acid is used as an active pharmaceutical ingredient for its anti-inflammatory and analgesic properties. It is particularly effective in treating conditions associated with inflammation and pain, such as arthritis and other musculoskeletal disorders.
Used in Chemical Synthesis:
In the field of chemical synthesis, (2-(2,6-Dichloro-4-hydroxyanilino)-5-hydroxyphenyl)acetic acid serves as a key intermediate in the production of various pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows for further functionalization and modification to create a wide array of compounds with diverse applications.
Used in Research and Development:
(2-(2,6-Dichloro-4-hydroxyanilino)-5-hydroxyphenyl)acetic acid is also utilized in research and development settings, where it can be employed as a probe or tool to study various biological processes and pathways. Its structural features make it a valuable candidate for investigating the interactions between small molecules and biological targets, such as enzymes, receptors, and other proteins.
Used in Material Science:
(2-(2,6-Dichloro-4-hydroxyanilino)-5-hydroxyphenyl)acetic acid may also find applications in the field of material science, particularly in the development of novel polymers and coatings with specific properties. Its functional groups can be exploited to create materials with enhanced mechanical, thermal, or chemical resistance, depending on the desired application.

InChI:InChI=1/C14H11Cl2NO4/c15-10-5-9(19)6-11(16)14(10)17-12-2-1-8(18)3-7(12)4-13(20)21/h1-3,5-6,17-19H,4H2,(H,20,21)

Upstream product

• 15307-86-5 [2-(2,6-dichloroanilino)phenyl]acetic acid 
• 15307-79-6 diclofenac sodium 
• 127792-39-6 <2-<(2,6-dichloro-4-methoxyphenyl)amino>-5-methoxyphenyl>glyoxylic acid 
• 127792-40-9 2-<(2,6-dichloro-4-methoxyphenyl)amino>-5-methoxyphenylacetic acid 
• 127792-37-4 N-(4-methoxyphenyl)-N-(2',6'-dichloro-4'-methoxyphenyl)oxaniloyl chloride 
• 136099-55-3 N-(2,6-dichloro-4-methoxyphenyl)acetamide 
• 127792-36-3 4'-methoxy-2,6-dichloro-4-methoxydiphenylamine 
• 6480-66-6 2,6-dichloro-4-methoxyaniline 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 245732-72-3 N-acetyl-N-(4-methoxyphenyl)-2,6-dichloro-4-methoxyaniline 
• 73328-72-0 1-(2,6-dichloro-4-hydroxyphenyl)-5-hydroxyoxindole 

Relevant academic research and scientific papers

Electrochemical oxidation of diclofenac on CNT and M/CNT modified electrodes

The electrochemical oxidation of diclofenac (DCF), a non-steroidal anti-inflammatory drug considered as an emerging pollutant (frequently detected in wastewater), was investigated on CNT, Pt/CNT and Ru/CNT modified electrodes based on Carbon Toray in aqueous media. The electroreactivity of DCF on these modified electrodes was studied using cyclic voltammetry and the kinetic parameters were calculated from the scan rate study. Cyclic voltammograms show several oxidation processes, which confirm the interaction between DCF and the catalyst surface necessary for direct oxidation processes. Constant potential electrolysis of DCF was carried out on carbon nanotubes (CNT) and metal supported CNT (M/CNT) modified electrodes, in 0.1 M NaOH and 0.1 M Na2CO3/NaHCO3buffer media. The highest DCF conversion (88% after 8 h of electrolysis) was found in carbonate buffer medium, for Ru/CNT, while the best carbon mineralization efficiency (corresponding to 48% of the oxidized DCF) was obtained on Pt/CNT modified electrode in 0.1 M NaOH medium. The products of the electrolyses were identified and quantified by HPLC-MS, GC-MS, HPLC-UV-RID and IC. The results show the presence of some low molecular weight carboxylic acids, confirming the cleavage of the aromatic rings during the oxidation process.

TiO2-modified MALDI target for in vitro modeling of the oxidative biotransformation of diclofenac

The UV-induced photocatalytic oxidation in the presence of TiO2 nanoparticles (UV/TiO2-PCO) is a more adequate approach than electrochemical oxidation to simulate the oxidative metabolism of diclofenac based on the comparative analysis of oxidation products using high-resolution tandem mass spectrometry. A simple and fast high-throughput technique is proposed for modeling the oxidative metabolism, which involves UV/TiO2-PCO performed directly on a MALDI target and subsequent analysis by matrix-assisted laser desorption/ionization mass spectrometry. The ranges and yields of diclofenac oxidation products obtained by the conventional bulk UV/TiO2-PCO and the proposed on-target version are in excellent agreement.

Degradation kinetics and mechanism of diclofenac by UV/peracetic acid

In this work, the degradation kinetics and mechanism of diclofenac (DCF) by UV/peracetic acid (PAA) was investigated. The effects of pH, PAA dose and common water components such as inorganic ions and dissolved organic matter (DOM) on DCF degradation by UV/PAA were also evaluated. It was observed that the addition of PAA promoted the photodegradation of DCF due to the generation of reactive radicals in the photolysis of PAA, which was also confirmed by the radical scavenging experiment. The best degradation efficiency of DCF was obtained at pH 8.5. The removal of DCF was enhanced gradually with increasing PAA dose. Since NO3- is a photosensitive substance which can generate HO under UV irradiation, its existence promoted the degradation of DCF. The presence of CO32- could slightly improve DCF degradation, which might be due to the role of generated carbonate radicals. Cl-, SO42- and Fe3+ had little effect on DCF removal, while Cu2+ could enhance DCF degradation because of its catalytic ability for PAA decomposition. An inhibition effect on DCF removal was observed in the presence of DOM, and it was more obvious in higher concentration of DOM. The elimination of total organic carbon (TOC) was low. According to the twelve reaction products detected in the UV/PAA system, the probable transformation mechanism of DCF was proposed exhibiting eight reaction pathways, i.e., hydroxylation, decarboxylation, formylation, dehydrogenation, dechlorination-hydrogenation, dechlorination-cyclization, dechlorination-hydroxylation and amidation. This study indicates that UV/PAA is a promising method for DCF removal from contaminated water.

Biobased Poly(ethylene furanoate) Polyester/TiO2 Supported Nanocomposites as Effective Photocatalysts for Anti-inflammatory/Analgesic Drugs

In the present study, polymer supported nanocomposites, consisting of bio-based poly(ethylene furanoate) polyester and TiO2 nanoparticles, were prepared and evaluated as effective photocatalysts for anti-inflammatory/analgesic drug removal. Nanocomposites were prepared by the solvent eVaporation method containing 5, 10, 15, and 20 wt% TiO2 and characterized using Fourier Transform Infrared spectroscopy (FTIR), differential scanning calorimetry (DSC), wide-angle X-ray diffraction (WAXD), thermogravimetric analysis (TGA), and scanning electron microscopy (SEM). Thin films of them have been prepared by the melt press and optimization of the photocatalytic procedure was conducted for the most efficient synthesized photocatalyst. Finally, mineralization was evaluated by means of Total organic carbon (TOC) reduction and ion release, while the transformation products (TPs) generated during the photocatalytic procedure were identified by high-resolution mass spectrometry.

Hepatic metabolism of diclofenac: Role of human CYP in the minor oxidative pathways

The aim of this study was to re-examine the human hepatic metabolism of diclofenac, with special focus on the generation of minor hydroxylated metabolites implicated in the idiosyncratic hepatotoxicity of the drug. Different experimental approaches were u

Synthesis and quantitative structure-activity relationships of diclofenac analogues

The synthesis of a series of 2-anilinophenylacetic acid, close analogues of diclofenac, is described. These compounds were tested in two models used for evaluating the activity of nonsteroidal antiinflammatory drugs (NSAID's), inhibition of cyclooxygenase enzyme activity in vitro, and adjuvant-induced arthritis (AdA) in rats. Statistically significant correlations were found between the inhibitory activities of the compounds in these two models, indicating that cyclooxygenase inhibition seems to be the underlying mechanism for the antiinflammatory activity of these compounds. Quantitative structure-activity relationship (QSAR) analysis revealed that the crucial parameters for activity in both models were the lipophilicity and the angle of twist between the two phenyl rings. Optimal activities were associated with halogen or alkyl substituents in both ortho positions of the anilino ring. Compounds with OH groups in addition to two ortho substituents or compounds with only one or no ortho substituents were less active.