1562-34-1

Basic information

• Product Name: PHENYL VINYLSULFONATE
• Synonyms: PHENYL VINYLSULFONATE;PHENYL ETHYLENESULFONATE;VINYLSULFONIC ACID PHENYL ESTER;Phenyl ethylenesulfonate, Vinylsulfonic acid phenyl ester;Ethene-1-sulfonic acid phenyl ester;Ethenesulfonic acid phenyl ester;Phenyl ethenesulfonate;Phenyl vinylsulfonate 95%
• CAS NO: 1562-34-1
• Molecular Formula: C₈H₈O₃S
• Molecular Weight: 184.21
• Mol File: 1562-34-1.mol

Chemical Properties

• Melting Point: 38-42 °C(lit.)
• Boiling Point: 44-46 °C2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.3761 (rough estimate)
• Vapor Pressure: 0.559mmHg at 25°C
• Refractive Index: 1.5151 (estimate)
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• Stability: Light Sensitive
• BRN: 2044718
• CAS DataBase Reference: PHENYL VINYLSULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYL VINYLSULFONATE(1562-34-1)
• EPA Substance Registry System: PHENYL VINYLSULFONATE(1562-34-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• RIDADR: 1759
• WGK Germany: 3
• F: 8
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 1562-34-1(Hazardous Substances Data)

Usage

Uses

1. Used in Chemical Synthesis:
Phenyl vinylsulfonate is used as a reactant for the synthesis of various chemical compounds, particularly in the formation of cycloadducts with alkyl furan derivatives. This application is due to its reactivity and ability to form stable products with a wide range of substrates.
2. Used in Catalyst Development:
Phenyl vinylsulfonate is used as a precursor in the development of palladium complexes, which are essential catalysts in various chemical reactions. The application reason is its ability to undergo a tetraphosphine-catalyzed Heck vinylation, leading to the formation of a palladium complex with potential catalytic properties.
3. Used in Pharmaceutical Research:
Phenyl vinylsulfonate may be used as a starting material or intermediate in the development of new pharmaceutical compounds. The application reason is its unique chemical structure, which can be further modified or functionalized to create novel drug candidates with potential therapeutic applications.
4. Used in Material Science:
Phenyl vinylsulfonate can be utilized in the development of new materials with specific properties, such as polymers with tailored characteristics. The application reason is its ability to undergo various chemical reactions, allowing for the creation of a diverse range of materials with different properties and potential applications.
5. Used in Environmental Applications:
Phenyl vinylsulfonate may be employed in the development of environmentally friendly processes or products, such as green chemistry applications. The application reason is its potential to be used as a building block for more sustainable chemical processes, reducing the environmental impact of certain industrial activities.

InChI:InChI=1/C8H8O3S/c1-2-12(9,10)11-8-6-4-3-5-7-8/h2-7H,1H2

Upstream product

• 6608-47-5 vinylsulfonyl chloride 
• 139-02-6 sodium phenoxide 
• 108-95-2 phenol 
• 1622-32-8 2-Chloroethanesulfonyl chloride 

Downstream Products

• 3058-82-0 4-chlorophenyl ethenesulfonate 
• 33912-50-4 4-Phenoxysulfonyl-cyclohex-1-en 
• 1562-37-4 β-<1-Nitro-cyclohexyl>-aethansulfonsaeure-phenylester 
• 133777-83-0 methyl α-<2-(phenoxysulfonyl)ethyl>benzeneacetate 
• 133777-86-3 4-Phenoxysulfonyl-2-(2-phenoxysulfonyl-ethyl)-2-phenyl-butyric acid methyl ester 
• 958298-04-9 7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-3-methoxy-6-(phenoxysulfonyl)-, 1,1-dimethylethyl ester 
• 172210-40-1 phenyl 2,2-dimethoxyethyl sulphonate 
• 91248-70-3 3-methyl-3-nitro-butane-1-sulfonic acid phenyl ester 
• 433961-87-6 2-{4-[4-((S)-2-Methyl-1-phenyl-propylcarbamoyl)-2-phenyl-quinolin-3-ylmethyl]-piperazin-1-yl}-ethanesulfonic Acid Phenyl Ester 

Relevant articles and documents

MILD AND PRACTICAL CYCLOADDITION REACTIONS OF FURANS WITH PHENYL VINYL SULFONATE

Phenyl vinyl sulfonate reacts with various alkyl furan derivatives under mild conditions to produce excellent yields of the corresponding cycloadducts.

Metal-free visible-light-promoted C(sp3)-H functionalization of aliphatic cyclic ethers using trace O2

Presented is a light-promoted C-C bond forming reaction yielding sulfone and phosphate derivatives at room temperature in the absence of metals or photoredox catalyst. This transformation proceeds in neat conditions through an auto-oxidation mechanism which is maintained through the leaching of trace amounts of O2 as sole green oxidant. This journal is

Novel Hybrid Conjugates with Dual Suppression of Estrogenic and Inflammatory Activities Display Significantly Improved Potency against Breast Cancer

In this work, we developed a small library of novel OBHS-RES hybrid compounds with dual inhibition activities targeting both the estrogen receptor α (ERα) and NF-?B by incorporating resveratrol (RES), a known inhibitor of NF-?B, into a privileged indirect antagonism structural motif (OBHS, oxabicycloheptene sulfonate) of estrogen receptor (ER). The OBHS-RES conjugates could bind well to ER and showed remarkable ERα antagonistic activity, and they also exhibited excellent NO inhibition in macrophage RAW 264.7 cells. Compared with 4-hydroxytamoxifen, some of them showed better antiproliferative efficacy in MCF-7 cell lines with IC50 up to 3.7 μM. In vivo experiments in a MCF-7 breast cancer model in Balb/c nude mice indicated that compound 26a was more potent than tamoxifen. Exploration of the compliancy of the structure against ER specificity utilizing these types of isomeric three-dimensional ligands indicated that one enantiomer had much better biological activity than the other.

Exploring Partners for the Domino α-Arylation/Michael Addition Reaction Leading to Tetrahydroisoquinolines

Sulfonates, sulfonamides, and phosphonates have proven useful nucleophiles for palladium-catalyzed intramolecular α-arylation reactions leading to tetrahydroisoquinolines. Although the sulfonate α-arylation reaction can be successfully combined in a domino process with a broad range of Michael acceptors, only vinyl sulfones can be used in Michael additions when starting from sulfonamides. No domino process was developed with the phosphonate derivative. DFT calculations were carried out to gain more insights into the experimental differences observed in the reactions involving these substrates.

Novel Bioactive Hybrid Compound Dual Targeting Estrogen Receptor and Histone Deacetylase for the Treatment of Breast Cancer

A strategy to develop chemotherapeutic agents by combining several active groups into a single molecule as a conjugate that can modulate multiple cellular pathways may produce compounds having higher efficacy compared to that of single-target drugs. In th

Identification and structure-activity relationships of a novel series of estrogen receptor ligands based on 7-thiabicyclo[2.2.1]hept-2-ene-7-oxide

To develop estrogen receptor (ER) ligands having novel structures and activities, we have explored compounds in which the central hydrophobic core has a more three-dimensional topology than typically found in estrogen ligands and thus exploits the unfilled space in the ligand-binding pocket. Here, we build upon our previous investigations of 7-oxabicyclo[2.2.1]heptene core ligands, by replacing the oxygen bridge with a sulfoxide. These new 7-thiabicyclo[2.2.1] hept-2-ene-7-oxides were conveniently prepared by a Diels-Alder reaction of 3,4-diarylthiophenes with dienophiles in the presence of an oxidant and give cycloadducts with endo stereochemistry. Several new compounds demonstrated high binding affinities with excellent ERα selectivity, but unlike oxabicyclic compounds, which are transcriptional antagonists, most thiabicyclic compounds are potent, ERα-selective agonists. Modeling suggests that the gain in activity of the thiabicyclic compounds arises from their endo stereochemistry that stabilizes an active ER conformation. Further, the disposition of methyl substituents in the phenyl groups attached to the bicyclic core unit contributes to their binding affinity and subtype selectivity.

Discovery of novel SERMs with a ferrocenyl entity based on the oxabicyclo[2.2.1]heptene scaffold and evaluation of their antiproliferative effects in breast cancer cells

We have synthesized a series of novel SERMs bearing a ferrocenyl unit based on a three-dimensional oxabicyclo[2.2.1]heptene core scaffold. These compounds displayed high receptor binding affinities as well as ERα or ERβ selectivity. In cell proliferation

Dioxygen mediated hydroacylation of vinyl sulfonates and sulfones on water

Herein we report a mild, facile method for the preparation of 1,4-keto-sulfonates and sulfones on water. Further synthetic manipulations can result in products that are not readily accessed by hydroacylation of electron rich alkenes.

PROCESS FOR PREPARATION OF NARATRIPTAN HYDROCHLORIDE

The present invention relates to an improved process for the preparation of N-methyl-3- (1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide hydrochloride of formula (I) having less than 0.15 % area by HPLC of 3-(1-methyl-4-piperidinyl)-1H-indole-5- ethanesulfonamide (1A) and intermediates thereof.