69002-86-4

Basic information

• Product Name: (2-(2,6-Dichloro-4-hydroxyanilino)-5-hydroxyphenyl)acetic acid
• Synonyms: (2-(2,6-Dichloro-4-hydroxyanilino)-5-hydroxyphenyl)acetic acid;4',5-Dihydroxydiclofenac;5-Hydroxy-2-(2,6-dichloro-4-hydroxyphenylamino)benzeneacetic acid;Benzeneacetic acid,2-[(2,6-dichloro-4-hydroxyphenyl)aMino]-5-hydroxy-;2-[2-(2,6-dichloro-4-hydroxyanilino)-5-hydroxyphenyl]acetic acid
• CAS NO: 69002-86-4
• Molecular Formula: C₁₄H₁₁Cl₂NO₄
• Molecular Weight: 328.15
• Mol File: 69002-86-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 465.4°C at 760 mmHg
• Flash Point: 235.2°C
• Appearance: /
• Density: 1.611g/cm³
• Vapor Pressure: 1.85E-09mmHg at 25°C
• Refractive Index: 1.718
• CAS DataBase Reference: (2-(2,6-Dichloro-4-hydroxyanilino)-5-hydroxyphenyl)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2-(2,6-Dichloro-4-hydroxyanilino)-5-hydroxyphenyl)acetic acid(69002-86-4)
• EPA Substance Registry System: (2-(2,6-Dichloro-4-hydroxyanilino)-5-hydroxyphenyl)acetic acid(69002-86-4)

Safety Data

• Hazardous Substances Data: 69002-86-4(Hazardous Substances Data)

Usage

Uses

4'',5-Dihydroxy Diclofenac is a metabolite of Diclofenac (D436450), a nonsteroidal anti-inflammatory compound and decycloxygenase (COX) inhibitor.

Definition

ChEBI: An monocarboxylic acid that is the 4',5-dihydroxylated metabolite of diclofenac.

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 articles and documents

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.

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.

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