24542-74-3

Basic information

• Product Name: 1-(2,6-Dichlorophenyl)indole-2,3-dione
• Synonyms: 1-(2,6-Dichlorophenyl)indole-2,3-dione;1-(2,6-Dichlorophenyl)indoline-2,3-dione;Diclofenac Related Compound 6
• CAS NO: 24542-74-3
• Molecular Formula: C₁₄H₇Cl₂NO₂
• Molecular Weight: 292.12
• Mol File: 24542-74-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 438.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.532±0.06 g/cm3(Predicted)
• PKA: -8.47±0.20(Predicted)
• CAS DataBase Reference: 1-(2,6-Dichlorophenyl)indole-2,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,6-Dichlorophenyl)indole-2,3-dione(24542-74-3)
• EPA Substance Registry System: 1-(2,6-Dichlorophenyl)indole-2,3-dione(24542-74-3)

Safety Data

• Hazardous Substances Data: 24542-74-3(Hazardous Substances Data)

Usage

Uses

N-(2,6-Dichlorophenyl)isatin can be obtained from 2,6-Dichloroiodobenzene (D434690) which is a reactant in the synthesis of 3-(phenoxy-phenyl-methyl)-pyrrolidines as potent and balanced norepinephrine and serotonin reuptake inhibitors. Also an impurity of Diclofenac (D436465).

Upstream product

• 24542-55-0 [(2,6-Dichloro-phenyl)-phenyl-amino]-oxo-acetyl chloride 
• 67-56-1 methanol 
• 15307-79-6 diclofenac sodium 
• 15307-93-4 N-phenyl-2,6-dichloroaniline 

Downstream Products

• 66156-75-0 2-(2-((2,6-dichlorophenyl)amino)phenyl)-2-oxoacetic acid 
• 121288-70-8 1-(2,6-Dichlorphenyl)-3-(dicyanmethylen)-2-indolon 
• 15307-79-6 diclofenac sodium 
• 66156-76-1 methyl 2-(2,6-dichloroanilino)phenylglyoxylate 
• 66867-42-3 ethyl 2-(2,6-dichloroanilino)phenylglyoxylate 
• 66867-40-1 methyl 2-(2,6-dichloroanilino)phenylglycolate 
• 66867-41-2 ethyl 2-(2,6-dichloroanilino)phenylglycolate 

Relevant articles and documents

The effect of humidity on the stability of diclofenac sodium in inclusion complex with β-cyclodextrin in the solid state

-

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.