4025-71-2

Basic information

• Product Name: 2-PHENYL-ETHANESULFONYL CHLORIDE
• Synonyms: 2-PHENYL-ETHANESULFONYL CHLORIDE;2-Phenyl-ethanesulfonyl chloride ,95%;2-phenylethane-1-sulfonyl chloride
• CAS NO: 4025-71-2
• Molecular Formula: C₈H₉ClO₂S
• Molecular Weight: 204.67
• Mol File: 4025-71-2.mol
• Article Data: 24

Chemical Properties

• Melting Point: 32-33 °C
• Boiling Point: 295.8 °C at 760 mmHg
• Flash Point: 132.7 °C
• Appearance: /
• Density: 1.323 g/cm³
• Vapor Pressure: 0.00262mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 2-PHENYL-ETHANESULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYL-ETHANESULFONYL CHLORIDE(4025-71-2)
• EPA Substance Registry System: 2-PHENYL-ETHANESULFONYL CHLORIDE(4025-71-2)

Safety Data

• RIDADR: 1759
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 4025-71-2(Hazardous Substances Data)

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

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

Downstream Products

• 1767-52-8 4-(4-benzyl-2,2-dimethyl-1,1-dioxo-1λ⁶-thietan-3-yl)-morpholine 
• 102834-58-2 2-Phenyl-ethanesulfonic acid p-tolyl ester 
• 102834-63-9 m-chlorophenyl 2-phenylethanesulfonate 
• 102834-61-7 2-Phenyl-ethanesulfonic acid 4-bromo-phenyl ester 
• 143769-62-4 2-Phenyl-ethanesulfonic acid (2,2-dimethyl-propyl)-amide 
• 13657-49-3 1,4-diphenylbut-2-ene 
• 126788-70-3 N,N-Dimethyl-2-phenyl-1-(2-phenylethyl-1-sulfonyl)ethansulfonamid 
• 76653-10-6 N-phenyl-β-phenethylsulfonamide 
• 95339-74-5 N-methyl-2-phenylethane-1-sulfonamide 
• 143769-72-6 (2-Phenyl-ethanesulfonylamino)-acetic acid ethyl ester 
• 16993-47-8 2-(phenyl)ethanesulfonamide 
• 102834-59-3 2-phenyl-ethanesulfonic acid phenyl ester 
• 1433543-50-0 N-hydroxy-2-(2-phenylethylsulfonamido)acetamide 
• 1156840-85-5 C₁₁H₁₅NO₄S 

Relevant articles and documents

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.

Convenient and environment-friendly synthesis of sulfonyl chlorides from S -alkylisothiourea salts via N-chlorosuccinimide chlorosulfonation

A convenient, practical, and environmentally friendly method for the synthesis of sulfonyl chlorides has been developed. Structurally diverse sulfonyl chlorides were synthesized in moderate to excellent yields from S-alkylisothiourea salts, which can be easily prepared from readily accessible alkyl halides or mesylates and inexpensive thiourea, via N-chlorosuccinimide chlorosulfonation. In large-scale syntheses, the byproduct succinimide from 'waste water' can be conveniently converted into the starting reagent N-chlorosuccinimide with sodium hypochlorite (bleach) to make the method sustainable. Georg Thieme Verlag Stuttgart, New York.