85829-14-7

Basic information

• Product Name: 2,4-Dichloro-5-nitroanisole
• Synonyms: 2,4-Dichloro-5-nitroanisole;1,5-Dichloro-2-methoxy-4-nitrobenzene
• CAS NO: 85829-14-7
• Molecular Formula: C₇H₅Cl₂NO₃
• Molecular Weight: 222.0255
• Mol File: 85829-14-7.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,4-Dichloro-5-nitroanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichloro-5-nitroanisole(85829-14-7)
• EPA Substance Registry System: 2,4-Dichloro-5-nitroanisole(85829-14-7)

Safety Data

• Hazardous Substances Data: 85829-14-7(Hazardous Substances Data)

Usage

Uses

2,4-Dichloro-5-nitroanisole is used in preparation of arylamines via reduction of nitroarenes.

Upstream product

• 553-82-2 1,3-dichloro-4-methoxybenzene 

Relevant articles and documents

Electrophilic Aromatic Substitution. Part 28. The Mechanism of Nitration of Some 4-Substituted Anisoles and Phenols, and of Rearrangement of the Intermediate 4-Nitro-4-substituted-cyclohexa-2,5-dienones

The kinetics of nitration in sulphuric acid of 2-chloro-4-methyl-, 4-chloro-, 2,4-dichloro-, and 4-fluoroanisole and of the corresponding phenols have been determined.The reaction products from the anisoles and from 2-chloro-4-methyl- and 4-fluoro-phenol have been determined.Results for 4-methylanisole supplementary to earlier ones are also reported.Generally the anisoles give the 2-nitro-derivatives and the 2-nitrophenols, and from 2-chloro-4-methylanisole, 2-chloro-4-methyl-4-nitrocyclohexa-2,5-dienone was formed as an intermediate.The decomposition of this dienone in sulphuric acid, like those of others, changes from a non-acid-catalysed to an acid-catalysed form with increasing acidity.The first form is regarded as a decomposition into an aryloxyl radical and nitrogen dioxide which can recombine to give the 2-nitrophenol.The formation of a small amount of 2-(4-fluorophenoxy)-4-fluorophenol in the nitration of 4-fluorophenol is seen as support for this view.The acid-catalysed form is regarded as the decomposition of the protonated dienone into a phenol-nitronium ion encounter-pair which can give the nitrophenol.A consequence of the mechanism is that if the phenol were nitrated at less than the encounter rate, the phenol itself would in appropriate conditions be a product of the ipso-nitration of the original anisole. 4-Methyl-, 2-chloro-4-methyl-, and 4-chloro-phenol have been so identified.Quantitative analysis of the results allows evaluation of the partitioning of dienone decomposition between the two modes.The mechanism accounts for the formation from 2,4-dichloro-anisole of both 2,4-dichloro-6- and 2,4-dichloro-5-nitroanisole, but only 2,4-dichloro-6-nitrophenol.