3996-47-2

Basic information

• Product Name: [(4-chlorophenyl)sulfinyl]acetic acid
• CAS NO: 3996-47-2
• Molecular Formula: C₈H₇ClO₃S
• Molecular Weight: 218.6574
• Mol File: 3996-47-2.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 444.3°C at 760 mmHg
• Flash Point: 222.5°C
• Density: 1.56g/cm³
• Vapor Pressure: 1.12E-08mmHg at 25°C
• Refractive Index: 1.658
• CAS DataBase Reference: [(4-chlorophenyl)sulfinyl]acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [(4-chlorophenyl)sulfinyl]acetic acid(3996-47-2)
• EPA Substance Registry System: [(4-chlorophenyl)sulfinyl]acetic acid(3996-47-2)

Safety Data

• Hazardous Substances Data: 3996-47-2(Hazardous Substances Data)

Usage

Description

[(4-chlorophenyl)sulfinyl]acetic acid is a chemical compound characterized by the molecular formula C8H7ClO3S. It is a derivative of sulfinylacetic acid, featuring a chlorine-substituted phenyl ring and a sulfinyl group attached to an acetic acid moiety. [(4-chlorophenyl)sulfinyl]acetic acid is known for its nucleophilic properties, which make it a versatile and significant component in organic chemistry.

Uses

Used in Organic Synthesis:
[(4-chlorophenyl)sulfinyl]acetic acid is utilized as a reagent in the field of organic synthesis, particularly for the formation of sulfonium compounds. Its unique structure and reactivity contribute to the synthesis of various complex organic molecules.
Used in Herbicide Development:
[(4-chlorophenyl)sulfinyl]acetic acid has been investigated for its potential application as a herbicide. The presence of the sulfinyl group endows it with specific chemical properties that could be harnessed to control the growth of unwanted plants, making it a candidate for further research and development in the agricultural industry.

Upstream product

• 3405-88-7 (4-chlorophenylthio)acetic acid 

Downstream Products

• 3405-89-8 2-(4-chloro-phenylsulfonyl)acetic acid 
• 92153-25-8 Bis-<4-chlor-phenylmercapto>-essigsaeure 
• 87298-94-0 (4-Chloro-benzenesulfinyl)-acetic acid; compound with 2-[bis-(2-hydroxy-ethyl)-amino]-ethanol 
• 98-57-7 4-chlorophenyl methyl sulfone 
• 934-73-6 methyl 4-chlorophenyl sulfoxide 

Relevant articles and documents

Alteration of electronic effect causes change in rate determining step: Oxovanadium(IV)–salen catalyzed sulfoxidation of phenylmercaptoacetic acids by hydrogen peroxide

Sulfoxidation of a series of phenylmercaptoacetic acids (PMAA) by hydrogen peroxide catalysed by oxovanadium(IV)–salen complexes has been carried out spectrophotometrically in 100% acetonitrile medium. The formation and involvement of hydroperoxovanadium(

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.

Modulation of catalytic activity by ligand oxides in the sulfoxidation of phenylmercaptoacetic acids by oxo(salen)chromium(V) complexes

Mechanism of sulfoxidation of eleven para-substituted phenyl mercaptoacetic acids (PMAAs) by three oxo(salen)chromium(V)+PF6?complexes in the presence of different ligand oxides (LOs) such as triphenylphosphine oxide, pyridine N-oxide and 4-picoline N-oxide have been studied spectrophotometrically in 100% acetonitrile medium. Spectral and kinetic profiles establish the formation of adduct, O[dbnd]Cr(V)(salen)+-LO as the reactive intermediate in the catalytic cycle. The rate of sulfoxidation is found to be enhanced significantly by the addition of LOs and introduction of substituent in PMAA and salen complex. Both electron releasing and electron withdrawing substituents in the substrate and oxidant facilitate the rate of sulfoxidation. Correlation with Hammett constants yields a non-linear concave upward curve. Based on the experimental results and substituent effects two different mechanisms, a direct oxygen atom transfer (DOT) for PMAAs with electron withdrawing substituents and a single electron transfer for PMAAs with electron donating substituents have been postulated.