24535-53-3

Basic information

• Product Name: Benzene, 1-chloro-4-[(4-nitrophenyl)sulfinyl]-
• CAS NO: 24535-53-3
• Molecular Formula: C12H8ClNO3S
• Molecular Weight: 281.719
• Mol File: 24535-53-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Benzene, 1-chloro-4-[(4-nitrophenyl)sulfinyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-chloro-4-[(4-nitrophenyl)sulfinyl]-(24535-53-3)
• EPA Substance Registry System: Benzene, 1-chloro-4-[(4-nitrophenyl)sulfinyl]-(24535-53-3)

Safety Data

• Hazardous Substances Data: 24535-53-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Benzene, 1-chloro-4-[(4-nitrophenyl)sulfinyl]is utilized as a reagent in organic synthesis, where its unique structure allows for the creation of a variety of complex organic molecules. Its reactivity and functional groups make it a versatile component in the synthesis of new compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Benzene, 1-chloro-4-[(4-nitrophenyl)sulfinyl]serves as a key building block for the synthesis of pharmaceutical drugs and related compounds. Its presence in drug synthesis is attributed to its ability to contribute to the development of molecules with specific therapeutic effects.
Used in Asymmetric Synthesis:
As a chiral sulfoxide, Benzene, 1-chloro-4-[(4-nitrophenyl)sulfinyl]is used in asymmetric synthesis, a field that focuses on the production of enantiomerically pure compounds. Its chiral center plays a crucial role in the creation of molecules with specific spatial arrangements, which is vital for the effectiveness and selectivity of pharmaceuticals.
Used in Biological and Pharmacological Research:
Benzene, 1-chloro-4-[(4-nitrophenyl)sulfinyl]has been studied for its potential biological and pharmacological properties. This research is aimed at understanding its interactions with biological systems and its potential use in the development of new therapeutic agents.

Upstream product

• 21969-11-9 1-(4-chlorophenylthio)-4-nitrobenzene 
• 106-54-7 p-Chlorothiophenol 
• 100-00-5 4-chlorobenzonitrile 

Downstream Products

• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 100-32-3 di(p-nitrophenyl) disulfide 
• 16096-86-9 p-chlorobenzenesulphinamide 
• 21969-11-9 1-(4-chlorophenylthio)-4-nitrobenzene 

Relevant articles and documents

Tetrabutylammonium tribromide impregnated MCM-48 as a heterogeneous catalyst for selective oxidation of sulfides

We report here tetrabutylammonium tribromide supported on MCM-48 as a highly efficient heterogeneous catalyst for the selective oxidation of sulfides, in ethanolic medium using hydrogen peroxide as an oxidant. The aforementioned oxidation reactions were found to proceed rapidly (20 min) and in good yield (85-99%) (17 examples). The oxidation products were characterized by 1H NMR, 13C NMR and elemental analysis. The catalytic properties were analysed by TEM, XRD and BET-surface area measurement. No over-oxidation of the substrates was observed (analysed by GC), and the catalyst was effectively recycled for five consecutive cycles without any significant loss in its catalytic activity.

Copper-Schiff base complex catalyzed oxidation of sulfides with hydrogen peroxide

A straightforward, efficient, and selective oxidation of sulfide to sulfoxide with 30% H2O2 catalyzed by copper(II)-Schiff base complex is described. The reactions proceed under mild conditions in acetonitrile at room temperature to provide a variety of aryl and alkyl sulfoxides in excellent yield.

Copper-Schiff base complex catalyzed oxidation of sulfides with hydrogen peroxide

A straightforward, efficient, and selective oxidation of sulfide to sulfoxide with 30% H2O2 catalyzed by copper(II)-Schiff base complex is described. The reactions proceed under mild conditions in acetonitrile at room temperature to provide a variety of aryl and alkyl sulfoxides in excellent yield.

Selective aerobic oxidation of sulfides to sulfoxides catalyzed by coenzyme NAD+ models

Coenzyme NAD+ models can be applied in the photooxygenation of sulfides to sulfoxides as organocatalysts at room temperature. A series of sulfoxides are synthesized easily with this protocol and the possible mechanism is discussed. This procedure provides a reliable approach to the clean production of useful sulfoxides in synthetic chemistry.

Kinetics and mechanism of oxygenation of aromatic sulfides and arylmercaptoacetic acids by peroxomonophosphoric acid

The oxygenation of aryl methyl sulfides and diaryl sulfides by peroxomonophosphoric acid in acetonitrile-water mixture follows an overall second-order kinetics, first-order in each reactant. The study of the influence of [H+] on the oxidation of phenyl methyl and diphenyl sulfides reveals that H2PO5- and HPO52- are the oxidising species in the oxidation process. In substituted phenyl methyl sulfides and diphenyl sulfides, the rate of oxygenation is accelerated by electron-donating substituents and retarded by electron-withdrawing groups, indicating the nucleophilic displacement by the sulfide sulfur on the peroxide oxygen. The negative ρ value obtained in the correlation analysis of rate constants with σ constants also shows the formation of a more positively charged sulfur species in the rate-limiting step. Studies with different alkyl phenyl sulfides (C6H5SR; R=Me, Et, Pri or But) indicate that the rate is retarded by bulky R groups. Similar kinetic results are also obtained in the peroxomonophosphoric acid oxidation of sodium phenylmercaptoacetate. On the basis of the kinetic studies, a common mechanism has been proposed.

CONVENIENT ONE-POT SYNTHESIS OF ARENESULFINAMIDES: REACTIONS OF 4-NITROPHENYL SUBSTITUTED PHENYL SULFOXIDES WITH ELEMENTAL SULFUR IN LIQUID AMMONIA

Various arenesulfinamides were synthesized in good yields by one-pot reactions of 4-nitrophenyl-substituted phenyl sulfoxides with elemental sulfur in liquid ammonia.The arenesulfinamides were further reduced with elemental sulfur in liquid ammonia to give corresponding disulfides.

VARIATION OF THE VALENCE OF SULFUR IN SUBSTITUTED 2,4-DINITROPHENYL PHENYL SULFOXIDES IN REARRANGEMENT PROCESSES

The oxidation of the bridging sulfur atom in diphenyl sulfides, leading to the formation of sulfoxides and sulfones, was investigated.The various rearrangement processes which occur in substituted 2,4-dinitrophenyl phenyl sulfoxides during electron impact and lead to the appearance of characteristic fragment ions were demonstrated.The effect of the nature of substituents on the main directions in mass-spectrometric dissociation was investigated, and a correlation was obtained between log Z'/Z for the fragment due to elimination of the bridging SO group from the molecular ion and the Hammett ? constants.