33358-47-3

Basic information

• Product Name: Benzoic acid, 3-nitro-2-(phenylthio)-, methyl ester
• CAS NO: 33358-47-3
• Molecular Formula: C14H11NO4S
• Molecular Weight: 289.312
• Mol File: 33358-47-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 3-nitro-2-(phenylthio)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 3-nitro-2-(phenylthio)-, methyl ester(33358-47-3)
• EPA Substance Registry System: Benzoic acid, 3-nitro-2-(phenylthio)-, methyl ester(33358-47-3)

Safety Data

• Hazardous Substances Data: 33358-47-3(Hazardous Substances Data)

Upstream product

• 93415-79-3 methyl 2-iodo-3-nitrobenzoate 
• 930-69-8 sodium thiophenolate 
• 5337-09-7 2-bromo-3-nitro-benzoic acid methyl ester 
• 53553-14-3 2-chloro-3-nitrobenzoic acid methyl ester 

Relevant articles and documents

Nucleophilic Substitution Reactions of 1-Halogeno-4-COR-2-nitrobenzenes and 1-Halogeno-6-COR-2-nitrobenzenes with Sodium Benzenethiolate and Piperidine. Can an "Inverted Built-in Solvation" Be Responsible for the Peculiar Activation by an o-Carboxamido Group in SNAr Reactions with an Anionic Nucleophile?

A kinetic study of the title reactions has allowed an interpretation of the higher efficiency of an o-carboxamido group with respect to an o-carbomethoxy group in activating the benzenethiolate-dehalogenation reactions in methanol (kCONH2/kCO2Me 2.2-3.0) as due to an interaction between the anionic nucleophile and the hydrogen atoms of the carboxamido group. An inversion of the activating power of the two groups (kCONH2/kCO2Me 0.14) in the reactions with the same nucleophile has been observed when they are in a para-position. Moreover, for piperidino-dehalogenation reactions in methanol kCONH2/kCO2Me ratios less than unity (0.2-0.6) have been observed independently of the position (ortho or para) of the carboxamido and carbomethoxy groups with respect to the reaction center.