3405-89-8

Usage

Uses

Used in Pharmaceutical Synthesis:
2-[(4-CHLOROPHENYL)SULFONYL]ACETIC ACID is used as a building block for the synthesis of various pharmaceuticals, due to its capacity to form biologically active molecules that can be utilized in the development of new drugs.
Used in Agrochemical Production:
In the agrochemical industry, 2-[(4-CHLOROPHENYL)SULFONYL]ACETIC ACID is used as a precursor in the synthesis of agrochemicals, contributing to the creation of compounds that can be employed in crop protection and other agricultural applications.
Used as a Sulfonylating Reagent:
2-[(4-CHLOROPHENYL)SULFONYL]ACETIC ACID is utilized as a sulfonylating reagent in various chemical reactions, facilitating the introduction of sulfonyl groups into target molecules, which can enhance their reactivity and properties.
Used in Anti-inflammatory and Analgesic Applications:
2-[(4-CHLOROPHENYL)SULFONYL]ACETIC ACID is used as an anti-inflammatory and analgesic agent, owing to its inherent properties that can help in reducing inflammation and alleviating pain.
Used in the Production of Nonsteroidal Anti-inflammatory Drugs (NSAIDs):
As a precursor, 2-[(4-CHLOROPHENYL)SULFONYL]ACETIC ACID is used in the manufacturing process of NSAIDs, which are widely used for their anti-inflammatory, analgesic, and antipyretic effects.
Used in the Development of Therapeutic Compounds:
2-[(4-CHLOROPHENYL)SULFONYL]ACETIC ACID is employed as a starting material in the research and development of new therapeutic compounds, potentially leading to the discovery of novel treatments for various medical conditions.

InChI:InChI=1/C8H7ClO4S/c9-6-1-3-7(4-2-6)14(12,13)5-8(10)11/h1-4H,5H2,(H,10,11)/p-1

Upstream product

• 3405-88-7 (4-chlorophenylthio)acetic acid 
• 14752-66-0 sodium p-chlorobenzenesulphinate 
• 3926-62-3 sodium monochloroacetic acid 
• 105-39-5 chloroacetic acid ethyl ester 
• 15446-25-0 methyl 4-chlorophenylsulphinylacetate 
• 52377-68-1 ethyl 2-(p-chlorophenylthio)acetate 
• 79-11-8 chloroacetic acid 
• 3996-47-2 4-Chlorophenylsulfenylacetic acid 
• 3636-65-5 ethyl 2-((4-chlorophenyl)sulfonyl)acetate 
• 106-54-7 p-Chlorothiophenol 

Downstream Products

• 3636-65-5 ethyl 2-((4-chlorophenyl)sulfonyl)acetate 
• 102582-97-8 (4-Chloro-benzenesulfonyl)-acetic acid; compound with 2-diethylamino-ethanol 
• 1854-83-7 α-(4-Chlor-benzol-sulfonyl)-styrol 
• 56267-65-3 2-Bromo-4-[(E)-2-(4-chloro-benzenesulfonyl)-vinyl]-1-methoxy-benzene 
• 86971-43-9 (E)-4-methylstyryl 4-chlorophenyl sulfone 
• 56267-73-3 (E)-1-(2-((4-chlorophenyl)sulfonyl)vinyl)-4-fluorobenzene 
• 6178-26-3 (E)-4-chlorostyryl 4-chlorophenyl sulfone 
• 16215-12-6 (E)-1-chloro-4-(styrylsulfonyl)benzene 
• 3406-65-3 E-4-methoxystyryl 4-chlorophenyl sulfone 

Relevant academic research and scientific papers

Modular Synthesis of Carbon-Substituted Furoxans via Radical Addition Pathway. Useful Tool for Transformation of Aliphatic Carboxylic Acids Based on "build-and-Scrap" Strategy

Utilizing radical chemistry, a new general C-C bond formation on the furoxan ring was developed. By taking advantage of the lability of furoxans, a wide variety of transformation of the synthesized furoxans have been demonstrated. Thus, this developed methodology enabled not only the modular synthesis of furoxans but also short-step transformations of carboxylic acids to a broad range of functional groups.

Synthesis and Pharmacological Activity of Tris(2-hydroxyethyl)ammonium 4-Chlorophenylsulfonylacetate

Methods for the synthesis of 4-chlorophenylsulfonylacetic acid and its tris(2-hydroxyethyl)ammonium salt (“sulfacetamine”) were studied. The results of in vitro and in vivo experiments showed that sulfacetamine possesses high antithrombotic, antioxidant, hypocholesterolemic, immunostimulating, and protective-adaptive activities.

Synthesis and antioxidant activity of bis unsaturated sulfones, bis pyrroles, and bis pyrazoles

The Michael acceptor 1,4-bis-(E)-2-(arylsulfonylvinyl)benzene was exploited to prepare a new series of bis heterocycles-(1,4-phenylene)bis(arylsulfonylpyrrole) and (1,4-phenylene)bis(arylsulfonyl pyrazole). All of the compounds were tested for antioxidant activity. Amongst the tested compounds, 1,4-bis-(E)-2-(arylsulfonylvinyl)benzene (5) was found to be the best potential antioxidant agent.

Discovery of 8-cyclopentyl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-7- oxo-7,8-dihydro-pyrido[2,3- d ]pyrimidine-6-carbonitrile (7x) as a potent inhibitor of cyclin-dependent kinase 4 (CDK4) and AMPK-related kinase 5 (ARK5)

The success of imatinib, a BCR-ABL inhibitor for the treatment of chronic myelogenous leukemia, has created a great impetus for the development of additional kinase inhibitors as therapeutic agents. However, the complexity of cancer has led to recent interest in polypharmacological approaches for developing multikinase inhibitors with low toxicity profiles. With this goal in mind, we analyzed more than 150 novel cyano pyridopyrimidine compounds and identified structure-activity relationship trends that can be exploited in the design of potent kinase inhibitors. One compound, 8-cyclopentyl-2-[4-(4-methyl- piperazin-1-yl)-phenylamino]-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6- carbonitrile (7x), was found to be the most active, inducing apoptosis of tumor cells at a concentration of approximately 30-100 nM. In vitro kinase profiling revealed that 7x is a multikinase inhibitor with potent inhibitory activity against the CDK4/CYCLIN D1 and ARK5 kinases. Here, we report the synthesis, structure-activity relationship, kinase inhibitory profile, in vitro cytotoxicity, and in vivo tumor regression studies by this lead compound.

Mass spectra of arylsulphonylacetic acids and correlation of fragment ions with substituent constants

The mass spectral studies of arylsulphonylacetic acids reveal that the skeletal rearrangement via aryl-oxygen bond formation is predominant with a weak competing alkyl migration.A linear correlation is obtained between the intensities of + ions, i.e. +> and the Hammett substituent constants.

SYNTHESIS OF ORGANOSULFONYLACETIC ACID

Alkylsulfonylacetic acids and their esters were obtained by the alcoholysis of alkyl β,β-dichlorovinyl sulfones and the oxidation of alkylthioacetic acids.Arylsulfonylacetic acids were synthesized by the reaction of sodium arenesulfinates with monochloroacetic acid.The optimum conditions for the reaction were obtained.Arylsulfonylacetic esters were obtained by the reaction of monochloroacetic esters with sodium arenesulfinate in DMFA, and their hydrolysis led to the corresponding acids with yields of 65-98percent.Dichloroacetic estersreacts with arenesulfinates, forming di(arylsulfonyl)acetic esters.

MODERN FRIEDEL-CRAFTS CHEMISTRY. XI. CYCLIZATION OF ARYL HALOALKYL SULFONES, ARYLSULFONYLACYL CHLORIDES AND THEIR CORRESPONDING SULFIDES

The sulfone group deactivation for cyclialkylation and cycliacylation reactions in the presence of Friedel-Crafts catalysts was demonstrated in a number of aryl chloroalkylsulfones (1-8) and arylsulfonylacyl chlorides (17a-22a), respectively.As expected, the corresponding arylchloroalkyl sulfides (9-16) and arylmercaptoacyl chlorides (13a-28a) underwent ring-closure reaction in most cases under the same conditions.The ease of cyclization was governed by the ring size, the stability of the attacking carbocation and the nucleophilicity of the aryl moiety.Also, the behaviour of benzyl sulfones (29, 31a, and 32a) and sulfides (33, 34a and 36a) was inconsistent.Noteworthy, the Friedel-Crafts cyclization reaction is thus considered an accessible method for the synthesis of compounds 37-41 and 45, 51.