19760-88-4

Basic information

• Product Name: Benzene, 1-ethoxy-4-(methylsulfonyl)-
• CAS NO: 19760-88-4
• Molecular Formula: C9H12O3S
• Molecular Weight: 200.258
• Mol File: 19760-88-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzene, 1-ethoxy-4-(methylsulfonyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-ethoxy-4-(methylsulfonyl)-(19760-88-4)
• EPA Substance Registry System: Benzene, 1-ethoxy-4-(methylsulfonyl)-(19760-88-4)

Safety Data

• Hazardous Substances Data: 19760-88-4(Hazardous Substances Data)

Upstream product

• 51094-45-2 (4-ethoxy-phenylsulfanyl)-acetic acid 
• 1614253-72-3 C₁₀H₁₂O₄S 
• 699-09-2 4-ethoxy-benzenethiol 
• 123-09-1 4-chlorophenyl methyl sulfide 
• 141-52-6 sodium ethanolate 
• 98-57-7 4-chlorophenyl methyl sulfone 
• 33733-78-7 1-ethoxy-4-methylsulfanyl-benzene 
• 106-46-7 para-dichlorobenzene 

Relevant articles and documents

Electrophilic and nucleophilic pathways in ligand oxide mediated reactions of phenylsulfinylacetic acids with oxo(salen)chromium(V) complexes

The mechanism of oxidative decarboxylation of phenylsulfinylacetic acids (PSAA) by oxo(salen)Cr(V)+ ion in the presence of ligand oxides has been studied spectrophotometrically in acetonitrile medium. Addition of ligand oxides (LO) causes a red shift in the λmax values of oxo(salen) complexes and an increase in absorbance with the concentration of LO along with a clear isobestic point. The reaction shows first-order dependence on oxo(salen)-chromium(V)+ ion and fractional-order dependence on PSAA and ligand oxide. Michaelis-Menten kinetics without kinetic saturation was observed for the reaction. The order of reactivity among the ligand oxides is picoline N-oxide > pyridine N-oxide > triphenylphosphine oxide. The low catalytic activity of TPPO was rationalized. Both electron-withdrawing and electron-donating substituents in the phenyl ring of PSAA facilitate the reaction rate. The Hammett plots are non-linear upward type with negative ρ value for electron-donating substituents, (ρ- = -0.740 to -4.10) and positive ρ value for electron-withdrawing substituents (ρ+ = +0.057 to +0.886). Non-linear Hammett plot is explained by two possible mechanistic scenarios, electrophilic and nucleophilic attack of oxo(salen)chromium(V)+-LO adduct on PSAA as the substituent in PSAA is changed from electron-donating to electron-withdrawing. The linearity in the log k vs. Eox plot confirms single-electron transfer (SET) mechanism for PSAAs with electron-donating substituents.

Spectral and mechanistic investigation of Oxidative Decarboxylation of Phenylsulfinylacetic Acid by Cr(VI)

The oxidative decarboxylation of phenylsulfinylacetic acid (PSAA) by Cr(VI) in 20% acetonitrile - 80% water (v/v) medium follows overall second order kinetics, first order each with respect to [PSAA] and [Cr(VI)] at constant [H+] and ionic strength. The reaction is acid catalysed, the order with respect to [H+] is unity and the active oxidizing species is found to be HCrO3+. The reaction mechanism involves the rate determining nucleophilic attack of sulfur atom of PSAA on chromium of HCrO3+ forming a sulfonium ion intermediate. The intermediate then undergoes a,β-cleavage leading to the liberation of CO2. The product of the reaction is found to be methyl phenyl sulfone. The operation of substituent effect shows that PSAA containing electron-releasing groups in the meta- and para-positions accelerate the reaction rate while electron withdrawing groups retard the rate. An excellent correlation is found to exist between log k2 and Hammett s constants with a negative value of reaction constant. The p value decreases with increase in temperature evidencing the high reactivity and low selectivity in the case of substituted PSAAs.