175435-38-8

Basic information

• Product Name: 4-chloro-3-fluoro-5-methoxynitrobenzene
• CAS NO: 175435-38-8
• Molecular Weight: 205.573
• Mol File: 175435-38-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-chloro-3-fluoro-5-methoxynitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-3-fluoro-5-methoxynitrobenzene(175435-38-8)
• EPA Substance Registry System: 4-chloro-3-fluoro-5-methoxynitrobenzene(175435-38-8)

Safety Data

• Hazardous Substances Data: 175435-38-8(Hazardous Substances Data)

Upstream product

• 3315-60-4 methanolate 
• 3828-41-9 2-chloro-1,3-difluoro-5-nitrobenzene 
• 658-07-1 2,6-Difluoro-4-nitrophenol 
• 124-41-4 sodium methylate 

Relevant articles and documents

Charge control in the S(N)Ar reaction. Meta substitution with respect to the activating nitro group in 3,4-dihalogenonitrobenzenes

The reactions of 3-fluoro-4-chloronitrobenzene and of 3,5-difluoro-4-chloronitrobenzene with thiophenoxide anion lead to predominant substitution of the chlorine atom through S(N)Ar orbital-controlled processes. However, when harder nucleophiles (methoxide anion) are used, the substitution of a fluorine atom meta with respect to the activating nitro group becomes apparent in the reaction of 3-fluoro-4-chloronitrobenzene, predominant in the reaction of 5-fluoro-4-chloro-3-methyoxynitrobenzene, and almost exclusive in the reaction of 3,5-difluoro-4-chloronitrobenzene. Kinetic measurements and theoretical calculations indicate that the observed meta substitution of a fluorine atom is a S(N)Ar charge-controlled reaction with a loosely bonded transition state.