4025-71-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Phenyl-ethanesulfonyl chloride is used as a key ingredient for the synthesis of various pharmaceutical products. Its reactivity with water and solubility in inorganic solvents make it a valuable component in the development of new medicines.
Used in Chemical Industry:
In the chemical industry, 2-Phenyl-ethanesulfonyl chloride is used as a raw material for the production of dyes and synthetic materials. Its unique properties contribute to the creation of a wide range of chemical products.
Used in Detergent Industry:
2-Phenyl-ethanesulfonyl chloride is used as a component in the formulation of detergents. Its properties help enhance the cleaning power and effectiveness of these products.
Used in Dye Industry:
In the dye industry, 2-Phenyl-ethanesulfonyl chloride is used as a precursor for the synthesis of various dyes. Its chemical properties contribute to the development of a diverse range of colorants for different applications.

InChI:InChI=1/C8H9ClO2S/c9-12(10,11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2

Upstream product

• 24521-57-1 S-phenethyl-isothiourea; hydrochloride 
• 35065-97-5 S-2-phenylethyl thioacetate 
• 34372-24-2 1-benzylthio-2-phenylethane 
• 89986-79-8 2-phenetyl sulfinyl chloride 
• 103-63-9 1-phenyl-2-bromoethane 
• 17356-08-0 thiourea 
• 60-12-8 2-phenylethanol 
• 6326-49-4 phenethyl carbamimidothioate hydrobromide 
• 28868-76-0 2-chlorodimethylmalonate 
• 13552-93-7 sodium 2-phenylethane-1-sulfonate 
• 100-41-4 ethylbenzene 
• 4410-99-5 2-mercaptophenylethane 
• 5654-72-8 2-phenylethyl thiocyanate 

Downstream Products

• 102834-61-7 2-Phenyl-ethanesulfonic acid 4-bromo-phenyl ester 
• 143769-61-3 N-hexyl 2-phenylethanesulfonamide 
• 143769-67-9 2-Phenyl-ethanesulfonic acid (4-phenyl-butyl)-amide 
• 76653-09-3 N-cyclohexyl-β-phenethylsulfonamide 
• 102834-60-6 2-Phenyl-ethanesulfonic acid 4-chloro-phenyl ester 
• 143769-64-6 2-Phenyl-ethanesulfonic acid phenethyl-amide 
• 143769-69-1 2-Phenyl-ethanesulfonic acid [2-(4-chloro-phenyl)-ethyl]-amide 
• 76653-10-6 N-phenyl-β-phenethylsulfonamide 
• 14182-67-3 2-methyl-4-phenyl-but-2-enoic acid ethyl ester 
• 622-24-2 2-phenylethyl chloride 
• 16993-47-8 2-(phenyl)ethanesulfonamide 
• 102834-59-3 2-phenyl-ethanesulfonic acid phenyl ester 

Relevant academic research and scientific papers

From off-to on-target: New BRAF-inhibitor-template-derived compounds selectively targeting mitogen activated protein kinase kinase 4 (MKK4)

The mitogen-activated protein kinase (MAP) kinase 4 (MKK4) was found to be a major regulator of liver regeneration and could be a valuable drug target addressing liver related diseases by restoring its intrinsic regenerative capacity. We report on the synthesis and optimization of novel MKK4 inhibitors following a target-hopping strategy from the FDA-approved BRAFV600E inhibitor PLX4032 (8). Applying an iterative multi-parameter optimization process we carved out essential structural features yielding in compounds with a low nanomolar affinity for MKK4 and excellent selectivity profiles against the main off-targets MKK7 and JNK1, which, upon relevant inhibition, would totally abrogate the pro-regenerative effect of MKK4 inhibition, as well as against the off-targets MAP4K5, ZAK and BRAF with selectivity factors ranging from 40 to 430 for our best-balanced compounds 70 and 73.

Enantioselective Hydroamination of Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer

An enantioselective, radical-based method for the intramolecular hydroamination of alkenes with sulfonamides is reported. These reactions are proposed to proceed via N-centered radicals formed by proton-coupled electron transfer (PCET) activation of sulfonamide N-H bonds. Noncovalent interactions between the neutral sulfonamidyl radical and a chiral phosphoric acid generated in the PCET event are hypothesized to serve as the basis for asymmetric induction in a subsequent C-N bond forming step, achieving selectivities of up to 98:2 er. These results offer further support for the ability of noncovalent interactions to enforce stereoselectivity in reactions of transient and highly reactive open-shell intermediates.

Searching for novel N1-substituted benzimidazol-2-ones as non-nucleoside HIV-1 RT inhibitors

Non-nucleoside reverse transcriptase inhibitors (NNRTIs) represent an integral part of the currently available combination antiretroviral therapy (cART) contributing to reduce the AIDS-mortality and turned the disease from lethal to chronic. In this conte

Structure Property Relationships of Carboxylic Acid Isosteres

The replacement of a carboxylic acid with a surrogate structure, or (bio)-isostere, is a classical strategy in medicinal chemistry. The general underlying principle is that by maintaining the features of the carboxylic acid critical for biological activity, but appropriately modifying the physicochemical properties, improved analogs may result. In this context, a systematic assessment of the physicochemical properties of carboxylic acid isosteres would be desirable to enable more informed decisions of potential replacements to be used for analog design. Herein we report the structure-property relationships (SPR) of 35 phenylpropionic acid derivatives, in which the carboxylic acid moiety is replaced with a series of known isosteres. The data set generated provides an assessment of the relative impact on the physicochemical properties that these replacements may have compared to the carboxylic acid analog. As such, this study presents a framework for how to rationally apply isosteric replacements of the carboxylic acid functional group.

Remote meta C-H bond functionalization of 2-phenethylsulphonic acid and 3-phenylpropanoic acid derivatives

This discovery illustrates selective meta C-H bond activation from multiple non-equivalent C-H bonds present in medicinally relevant arylethanesulfonic acid and the 2-arylpropanoic acid moiety using weakly coordinating nitrile as a directing group. Transformation of the meta olefinated compounds to important organic molecules has been demonstrated. Efforts were made to obtain mechanistic detail of the meta C-H bond functionalization reaction.

Towards Uniform Iodine Catalysis: Intramolecular C?H Amination of Arenes under Visible Light

A photochemical catalytic amination of arenes is presented. The reaction proceeds under benign iodine catalysis in the presence of visible light as the initiator and provides access to a range of differently substituted arylamines. A total of 29 examples demonstrate the broad applicability of this mild oxidation method. The scope of the reaction could further be expanded to silyl-tethered derivatives, which undergo intramolecular amination upon formation of seven-membered heterocycles. Cleavage of the silicon tether provides access to the corresponding 3-substituted anilines.

COMPOUNDS CAPABLE OF INHIBITING VOLTAGE GATED CALCIUM ION CHANNEL, AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME

Disclosed herein are an N-(pyrazolylmethyl)arylsulfonamide derivative useful as a calcium ion channel blocker, a pharmaceutically acceptable salt thereof, and the medicinal use thereof as a therapeutic agent using its calcium ion channel blocking effect.

Amines vs. N-Oxides as Organocatalysts for Acylation, Sulfonylation and Silylation of Alcohols: 1-Methylimidazole N-Oxide as an Efficient Catalyst for Silylation of Tertiary Alcohols

A comparison of the relative catalytic efficiencies of Lewis-basic amines vs. N-oxides for the acylation, sulfonylation and silylation of primary, secondary and tertiary alcohols is reported. Whilst the amines are generally superior to the N-oxides for acylation, the N-oxides are superior for sulfonylation and silylation. In particular, 1-methylimidazole N-oxide (NMI-O) is found to be a highly efficient catalyst for sulfonylation and silylation reactions. To the best of our knowledge, NMI-O is the first amine or N-oxide Lewis basic organocatalyst capable of promoting the efficient silylation of tert-alcohols in high yield with low catalyst loading under mild reaction conditions.

Discovery of a new class of potent MMP inhibitors by structure-based optimization of the arylsulfonamide scaffold

A new class of potent matrix metalloproteinase (MMP) inhibitors designed by structure-based optimization of the well-known arylsulfonamide scaffold is presented. Molecules show an ethylene linker connecting the sulfonamide group with the P1' aromatic portion and a D-proline residue bearing the zinc-binding group. The affinity improvement provided by these modifications led us to discover a nanomolar MMP inhibitor bearing a carboxylate moiety as zinc-binding group, which might be a promising lead molecule. Notably, a significant selectivity for MMP-8, MMP-12, and MMP-13 was observed with respect to MMP-1 and MMP-7.

Synthesis and receptor binding studies of novel 4,4-disubstituted arylalkyl/arylalkylsulfonyl piperazine and piperidine-based derivatives as a new class of σ1 ligands

This study presents the synthesis and biological evaluation of a new series of arylalkyl/arylalkylsulfonyl piperazine and piperidine-based derivatives as sigma receptor ligands. It was found that a number of halogen substituted sulfonamides display relatively high and low affinities to σ1 and σ2 receptors, respectively. The σ1 affinities and subtype selectivities of four piperidine derivatives were also found to be generally comparable to those of piperazine analogues. Compared to σ1-Rs compounds with n = 0 and 2, those with n = 1 proved to have optimal length of carbon chain by exhibiting higher affinities. Within this series, the 4-benzyl-1-(3-iodobenzylsulfonyl)piperidine sigma ligand was identified with 96-fold σ1/σ2 selectivity ratio (Kiσ1 = 0.96 ± 0.05 nM and K iσ2 = 91.8 ± 8.1 nM).