27204-57-5

Basic information

• Product Name: (2-(2,6-DICHLOROANILINO)PHENYL) METHANOL
• Synonyms: [2-[(2,6-DICHLOROPHENYL)AMINO]PHENYL]-METHANOL;(2-(2,6-DICHLOROANILINO)PHENYL) METHANOL;DICLOFENAC ALCOHOL;2-[(2,6-Dichlorophenyl)amino]benzenemethanol;o-(2,6-dichloroanilino)benzyl Alcohol;[2-[(2,6-Dichlorophenyl)amino]phenyl]methanol (Diclofenac Impurity);Diclofenac Alcohol (Diclofenac IMpurity);Diclofenac iMpurity C
• CAS NO: 27204-57-5
• Molecular Formula: C₁₃H₁₁Cl₂NO
• Molecular Weight: 268.14
• Product Categories: Aromatics;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 27204-57-5.mol

Chemical Properties

• Melting Point: 109-111?C
• Boiling Point: 366.7°C at 760 mmHg
• Flash Point: 175.6°C
• Appearance: /
• Density: 1.387g/cm³
• Vapor Pressure: 5.05E-06mmHg at 25°C
• Refractive Index: 1.666
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly, Heated), Methanol
• PKA: 14.06±0.10(Predicted)
• CAS DataBase Reference: (2-(2,6-DICHLOROANILINO)PHENYL) METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (2-(2,6-DICHLOROANILINO)PHENYL) METHANOL(27204-57-5)
• EPA Substance Registry System: (2-(2,6-DICHLOROANILINO)PHENYL) METHANOL(27204-57-5)

Safety Data

• Hazardous Substances Data: 27204-57-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2-(2,6-DICHLOROANILINO)PHENYL) METHANOL is used as an impurity in the production of Diclofenac, a nonsteroidal anti-inflammatory drug (NSAID). It serves as a crucial component in the synthesis process, contributing to the overall effectiveness and quality of the final product.
Used in Anti-inflammatory Applications:
As a derivative of Diclofenac, (2-(2,6-DICHLOROANILINO)PHENYL) METHANOL may also possess anti-inflammatory properties, making it potentially useful in the development of new medications or therapies for various inflammatory conditions. However, further research and development would be required to explore and confirm these potential applications.
Used in Quality Control and Analysis:
In the pharmaceutical industry, (2-(2,6-DICHLOROANILINO)PHENYL) METHANOL can be used as a reference compound for quality control and analysis purposes. It can help ensure the purity and consistency of Diclofenac products by serving as a benchmark for comparison during testing and evaluation processes.
Used in Research and Development:
(2-(2,6-DICHLOROANILINO)PHENYL) METHANOL can be utilized in research and development efforts to better understand the chemical properties and potential applications of related compounds. This knowledge can lead to the discovery of new drugs or therapies, as well as improvements in the synthesis and production of existing medications.

InChI:InChI=1/C13H11Cl2NO/c14-10-5-3-6-11(15)13(10)16-12-7-2-1-4-9(12)8-17/h1-7,16-17H,8H2

Upstream product

• 15307-79-6 diclofenac sodium 
• 13625-57-5 diclofenac 
• 608-31-1 2,6-Dichloroaniline 
• 118-91-2 ortho-chlorobenzoic acid 
• 54616-46-5 2-Iodo-N,N-dimethylbenzamide 
• 51225-04-8 2-(2,6-dichloro-phenylamino)-N,N-dimethyl-benzamide 

Downstream Products

• 27204-58-6 α-chloro-N-(2,6-dichlorophenyl)-o-toluidine 
• 269061-87-2 dimethyl 2-(2',6'-dichloroanilino)phenylmethylphosphonate 

Relevant articles and documents

Oxidation of diclofenac sodium by diperiodatoargantate(III) in aqueous alkaline medium and its determination in urine and blood by kinetic methods

The kinetics and oxidation of diclofenac sodium (DFS) by diperiodatoargentate(III) (DPA) in alkaline medium at 298 K and at a constant ionic strength of 0.60 mol dm-3 were studied spectrophotometrically. The oxidation products were [2-(2,6-dicloro-phynylamino)- phenyl]-methenol and Ag(I), identified by LC-ESI-MS and IR spectral studies. The reaction between DFS and DPA in alkaline medium exhibits 1:1 stoichiometry. The reaction is first order in [DPA] and has a less than unit order dependence each in [DFS] and [alkali]. Increasing concentrations of IO4- retard the reaction. The active species of DPA proposed to be monoperi- odatoargentate(III), and a mechanism is suggested. The rate constants involved in the different steps of the mechanism were determined and are discussed. The activation parameters with respect to a rate-limiting step of the mechanism were determined. The thermodynamic quantities were also determined. Using the oxidation of DFS by DPA, DFS was analyzed by kinetic methods in urine and blood sample. The proposed method enables DFS analysis in the range from 5.0 × 10-5 to 5.0 x 10-3 mol dm-3.

Kinetics and mechanism of oxidation of diclofenac sodium by Keggin type 12-tungstocobalt(III) in aqueous medium

The kinetics of electron transfer reaction of diclofenac sodium with 12-tungstocobaltate (III) complex has been studied spectrophotometrically over the range 2.0 × 10-3 ≤ [diclofenac sodium] ≤ 6.0 × 10-3 mol/L, 6.03 ≤ pH ≤ 8.0 and at 293 ≤ T ≤ 308 K in aqueous medium at constant ionic strength I (0.5 mol/L sodium perchlorate). The electron transfer reaction showed pseudo-first order dependence in [diclofenac sodium] and [12-tungstocobaltate(III)] and less than unit order in [OH–]T. The activation parameters calculated for the electron transfer reaction favoured the formation of a precursor complex between the reactants. The product is characterized by FTIR and NMR spectra and is found to be [2-(2,6-dichloro phenylamino)phenyl]methanol.

Spectral and mechanistic investigation of the osmium(VIII) catalyzed oxidation of diclofenac sodium by the copper(III) periodate complex in aqueous alkaline medium

The kinetics of the osmium(VIII) (Os(VIII)) catalyzed oxidation of diclofenac sodium (DFS) by diperiodatocuprate(III) (DPC) in aqueous alkaline medium has been studied spectrophotometrically at a constant ionic strength of 1.0 mol·dm-3. The reaction showed first order kinetics in [Os(VIII)] and [DPC] and less than unit order with respect to [DFS] and [alkali]. The rate decreased with increase in [periodate]. The reaction between DFS and DPC in alkaline medium exhibits 1:2 [DFS]:[DPC] stoichiometry. However, the order in [DFS] and [OH-] changes from first order to zero order as their concentration increases. Changes in the ionic strength and dielectric constant did not affect the rate of reaction. The oxidation products were identified by LC-ESI-MS, NMR, and IR spectroscopic studies. A possible mechanism is proposed. The reaction constants involved in the different steps of the mechanism were calculated. The catalytic constant (K C) was also calculated for Os(VIII) catalysis at the studied temperatures. From plots of log∈10 K C versus 1/T, values of activation parameters have been evaluated with respect to the catalytic reaction. The activation parameters with respect to the slow step of the mechanism were computed and discussed, and thermodynamic quantities were also determined. The active osmium(VIII) and copper(III) periodate species have been identified.

Phosphonic acid analogs of diclofenac: An Arbuzov reaction of trimethylphosphite with an ortho-quinonoid intermediate

The phosphonic acid analog of the NSAID Diclofenac was efficiently synthesized via an Arbuzov reaction between 2-(2,6-dichloroanilino)benzyl alcohol and trimethyl phosphite followed by TMSBr promoted dealkylation. Seven related phosphonic acids were synth

Stability of diclofenac sodium in the inclusion complex with β-cyclodextrin in the solid state

The aim of this study was to characterize the thermal stability of diclofenac sodium both alone and in the inclusion complex with β-cyclodextrin in the solid state, by determination of the number of the products of its decomposition, which were identified by GC-MS. The molar ratio of diclofenac sodium in the inclusion complex with β-cyclodextrin was 1:1. The decomposition of diclofenac sodium both alone and in inclusion complex with β-cyclodextrin occurred according to the first-order reaction. The HPLC of the samples thermostated at 80°C gave five products of decomposition, which were identified by GC-MS. Diclofenac sodium in the inclusion complex with β-cyclodextrin was more thermally stable. Thermal decomposition of diclofenac sodium leads to formation of five products, of which 4-chloro-10H-9-acridinone had not been reported previously in the literature.