22017-57-8

Basic information

• Product Name: ethyl 4-methoxybenzenesulfonate
• Synonyms: Benzenesulfonic acid, 4-methoxy-, ethyl ester
• CAS NO: 22017-57-8
• Molecular Formula: C₉H₁₂O₄S
• Molecular Weight: 216.2542
• Mol File: 22017-57-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 324.2°C at 760 mmHg
• Flash Point: 149.9°C
• Density: 1.214g/cm³
• Vapor Pressure: 0.000472mmHg at 25°C
• Refractive Index: 1.506
• CAS DataBase Reference: ethyl 4-methoxybenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4-methoxybenzenesulfonate(22017-57-8)
• EPA Substance Registry System: ethyl 4-methoxybenzenesulfonate(22017-57-8)

Safety Data

• Hazardous Substances Data: 22017-57-8(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 98-68-0 4-methoxy-phenyl-sulphonyl chloride 
• 141-52-6 sodium ethanolate 
• 100-66-3 methoxybenzene 
• 64-67-5 diethyl sulfate 
• 696-63-9 4-Methoxybenzenethiol 
• 51-28-5 2,4-Dinitrophenol 
• 917-58-8 potassium ethoxide 
• 154853-46-0 2,4-dinitrophenyl 4-methoxybenzenesulfonate 

Relevant articles and documents

Electrochemical synthesis of sulfinic esters from alcohols and thiophenols

Electrochemical oxidative couplings between S[sbnd]H and O[sbnd]H bonds are achieved herein directly from readily-available alcohols and thiophenols, affording a series of diverse sulfinic esters. This strategy can take advantage of 6 equivalents of alcohol, relative to thiophenol, to achieve moderate to good yields, without the assistance of any metallic catalysts, bases, and additional oxidants.

Synthesis and reactivity of phosphine-arenesulfonate palladium(II) alkyl complexes that contain methoxy substituents

Phosphine-arenesulfonate ligands that contain 1-3 methoxy substituents on the benzo linker, P(2-OMe-Ph)2(2-SO3Na-5-OMe-Ph) (Na[1a]), P(2-MeO-Ph)2(2-SO3Na-4,5-(OMe)2-Ph) (Na[1b]) and P(2-MeO-Ph)2

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.