3996-48-3

Basic information

• Product Name: [(4-bromophenyl)sulfinyl]acetic acid
• CAS NO: 3996-48-3
• Molecular Formula: C₈H₇BrO₃S
• Molecular Weight: 263.1084
• Mol File: 3996-48-3.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 460.8°C at 760 mmHg
• Flash Point: 232.5°C
• Density: 1.86g/cm³
• Vapor Pressure: 2.75E-09mmHg at 25°C
• Refractive Index: 1.694
• CAS DataBase Reference: [(4-bromophenyl)sulfinyl]acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [(4-bromophenyl)sulfinyl]acetic acid(3996-48-3)
• EPA Substance Registry System: [(4-bromophenyl)sulfinyl]acetic acid(3996-48-3)

Safety Data

• Hazardous Substances Data: 3996-48-3(Hazardous Substances Data)

Usage

Description

[(4-bromophenyl)sulfinyl]acetic acid, also known as N-Acetyl-S-(4-bromophenyl)-L-cysteine, is a chemical compound characterized by the molecular formula C10H9BrO3S. It is a sulfone derivative of acetic acid, featuring a bromo-phenyl group attached to a sulfinyl functional group. [(4-bromophenyl)sulfinyl]acetic acid is recognized for its utility as a precursor in the synthesis of a variety of pharmaceuticals and organic compounds, and it holds potential in the realm of medicinal chemistry. Careful handling is advised due to the possible health risks associated with improper handling.

Uses

Used in Pharmaceutical Synthesis:
[(4-bromophenyl)sulfinyl]acetic acid is utilized as a key precursor in the creation of various pharmaceuticals. Its unique structural features allow for its incorporation into a range of medicinal compounds, contributing to the development of new drugs and therapies.
Used in Organic Chemistry:
In the field of organic chemistry, [(4-bromophenyl)sulfinyl]acetic acid serves as an important building block for synthesizing complex organic molecules. Its versatility in reactions makes it a valuable component in organic synthesis processes.
Used in Medicinal Chemistry:
[(4-bromophenyl)sulfinyl]acetic acid also holds promise in medicinal chemistry, where it may be employed to design and develop novel therapeutic agents. Its structural properties could be harnessed to create molecules with specific biological activities, potentially leading to advancements in the treatment of various diseases and conditions.

Upstream product

• 3406-76-6 (4-bromophenylthio)acetic acid 
• 106-53-6 para-bromobenzenethiol 

Downstream Products

• 63216-00-2 p-bromophenylsulfinylacetic acid methyl ester 
• 80214-19-3 p-bromophenylsulfinylacetic acid p-bromophenacyl ester 
• 80214-23-9 p-bromophenylsulfinylacetic acid p-nitrobenzyl ester 
• 80214-17-1 p-bromophenylsulfinylacetic acid amide 
• 3466-32-8 4-bromoohenyl methyl sulfone 
• 934-71-4 1-bromo-4-(methylsulfinyl)benzene 

Relevant articles and documents

Competitive behavior of nitrogen based axial ligands in the oxovanadium(IV)-salen catalyzed sulfoxidation of phenylmercaptoacetic acid

The sulfoxidation of twelve phenylmercaptoacetic acids (PMAA) by H2O2 catalyzed by three oxovanadium(IV)-salen complexes, having varied substituents on PMAA and salen with regard to their position, size and inductive effect, has been performed spectrophotometrically in 100percent acetonitrile medium. Three nitrogen bases (NB), pyridine (Py), imidazole (ImH) and 1-methylimidazole (MeIm), were used as axial ligands. It has been found that the rate of sulfoxidation is not only tuned by the substituents on PMAA and salen, but it is also varied by the addition of nitrogen bases. The observed order of retardation found among the different nitrogen bases is ImH > MeIm > Py. The rate of reaction decreases with the increase in concentration of the NB axial ligands. The strongly binding ImH shows the least reactivity. Hydroperoxovanadium(V)-salen has been proposed as the sole active oxidizing species. A detailed mechanistic study reveals that the low rate constant values in the presence of the nitrogen base is due to the existence of competition of NB with H2O2 and PMAA during the formation of active species and the coordination of PMAA with active species, respectively. Both electron donating and electron withdrawing substituents on PMAA retard the sulfoxidation rate significantly. The Hammett correlation between the rate constants and substituent constants shows a non-linear concave downward curve which is explained by the existence of two different rate determining steps within the same mechanism; coordination of PMAA with the active species for electron withdrawing substituents and transfer of oxygen to PMAA for electron donating substituents. All the experimental observations are explained by proposing a suitable mechanism.

Importance of ground state stabilization in the oxovanadium(IV)-salophen mediated reactions of phenylsulfinylacetic acids by hydrogen peroxide – Non-linear Hammett correlation

A systematic study on the oxidative decarboxylation of a series of phenylsulfinylacetic acids (PSAA) by hydrogen peroxide with four oxovanadium(IV)-salophen catalysts in 100% acetonitrile medium is presented. The hydroperoxovanadium(V)-salophen generated from the reaction mixture is identified as the bonafide active oxidizing species. Introduction of electron donating groups (EDG) in the oxovanadium(IV)-salophen catalyst and electron withdrawing groups (EWG) in PSAA enhances the reactivity, whereas EWG in the catalyst and EDG in PSAA have a retarding effect on the reaction. A Hammett correlation displays a non-linear downward curvature, which consists of two intersecting straight lines and the ρ value shifts from small positive to moderately high as the substituents change from EWG to EDG. The importance of the ground state stabilization of PSAA is inferred from a linear Yukawa–Tsuno plot. Based on the observed substituent effects and the spectral changes, a mechanism involving electrophilic attack of PSAA on the nucleophilic peroxo oxygen atom of the vanadium complex in the rate determining step followed by oxygen atom transfer is proposed.

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.