3256-78-8

Basic information

• Product Name: ethyl 3-nitrobenzenesulfonate
• Synonyms: ethyl 3-nitrobenzenesulfonate
• CAS NO: 3256-78-8
• Molecular Weight: 231.229
• Mol File: 3256-78-8.mol

Chemical Properties

• CAS DataBase Reference: ethyl 3-nitrobenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-nitrobenzenesulfonate(3256-78-8)
• EPA Substance Registry System: ethyl 3-nitrobenzenesulfonate(3256-78-8)

Safety Data

• Hazardous Substances Data: 3256-78-8(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 38205-95-7 N-isopropylidene-3-nitrobenzenesulfenamide 
• 51-28-5 2,4-Dinitrophenol 
• 121-51-7 3-nitrobenzenesulphonyl chloride 
• 156839-99-5 2,4-dinitrophenyl 3-nitrobenzenesulfonate 
• 917-58-8 potassium ethoxide 

Downstream Products

• 121-47-1 3-aminobenzenesulfonic acid 

Relevant articles and documents

A kinetic study on nucleophilic displacement reactions of aryl benzenesulfonates with potassium ethoxide: Role of K+ ion and reaction mechanism deduced from analyses of LFERs and activation parameters

Pseudofirst-order rate constants (kobsd) have been measured spectrophotometrically for the nucleophilic substitution reactions of 2,4-dinitrophenyl X-substituted benzenesulfonates 4a-f and Y-substituted phenyl benzenesulfonates 5a-k with EtOK in anhydrous ethanol. Dissection of k obsd into kEtO- and kEtOK (i.e., the second-order rate constants for the reactions with the dissociated EtO - and ion-paired EtOK, respectively) shows that the ion-paired EtOK is more reactive than the dissociated EtO-, indicating that K + ion catalyzes the reaction. The catalytic effect exerted by K + ion (e.g., the kEtOK/kEtO- ratio) decreases linearly as the substituent X in the benzenesulfonyl moiety changes from an electron-donating group (EDG) to an electron-withdrawing group (EWG), but it is independent of the electronic nature of the substituent Y in the leaving group. The reactions have been concluded to proceed through a concerted mechanism from analyses of the kinetic data through linear free energy relationships (e.g., the Bronsted-type, Hammett, and Yukawa-Tsuno plots). K+ ion catalyzes the reactions by increasing the electrophilicity of the reaction center through a cyclic transition state (TS) rather than by increasing the nucleofugality of the leaving group. Activation parameters (e.g., ΔH? and ΔS?) determined from the reactions performed at five different temperatures further support the proposed mechanism and TS structures.

Chemistry of Oxaziridines. 1. Synthesis and Structure of 2-Arenesulfonyl-3-aryloxaziridines. A New Class of Oxaziridines

A new class of oxaziridine derivatives, 2-arenesulfonyl-3-aryloxaziridines (2), is prepared by m-CPBA oxidation of sulfonimines (RSO2N=CHAr).These compounds are the first stable examples of this ring system to have a substituent other than carbon attached to nitrogen and are characterized by a highly electrophilic oxaziridine oxygen atom.These oxaziridines have the E configuration as determined by X-ray crystallography.The presence of the powerful electron-attracting sulfonyl group attached to nitrogen apparently has little effect on the structure of the oxaziridine three-membered ring.Of more significance are the observations that the nitrogen lone pair in 2 is opposite to one of the sulfonyl oxygens and that the long S-N bond length implies little if any conjugative interaction between sulfur and nitrogen.Attempts to prepare oxaziridines via oxidation of sulfonimines, 5, derived from acetophenone gave imidoyl ether 14, a novel Baeyer-Villiger oxidation product of a C-N double bond.