Phenyl vinyl sulfone

Base Information

• Chemical Name: Phenyl vinyl sulfone
• CAS No.: 5535-48-8
• Molecular Formula: C8H8O2S
• Molecular Weight: 168.216
• Hs Code.: 29309090
• European Community (EC) Number: 226-890-2
• NSC Number: 35394
• UNII: 31973457VY
• DSSTox Substance ID: DTXSID50203903
• Nikkaji Number: J102.264D
• Wikidata: Q27256031
• ChEMBL ID: CHEMBL165058
• Mol file: 5535-48-8.mol

Synonyms:phenyl vinyl sulfone;PVS cpd

Chemical Property of Phenyl vinyl sulfone

Chemical Property:

• Appearance/Colour: off-white or tan powder
• Vapor Pressure: 0.000864mmHg at 25°C
• Melting Point: 67-69 °C(lit.)
• Refractive Index: 1.536
• Boiling Point: 314.4 °C at 760 mmHg
• Flash Point: 178.6 °C
• PSA: 42.52000
• Density: 1.177 g/cm³
• LogP: 2.68460
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: It is soluble in most common organic solvents.
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 168.02450067
• Heavy Atom Count: 11
• Complexity: 217

Purity/Quality:

99% ^*data from raw suppliers

Phenyl vinyl sulfone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-43-41-37/38-22
• Safety Statements: 26-36/37/39-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CS(=O)(=O)C1=CC=CC=C1
• General Description: **Phenyl vinyl sulfone** is a reactive Michael acceptor used in asymmetric Michael reactions to synthesize chiral β-ketophosphonates and in the preparation of 3-substituted-4-hydroxyquinoline N-oxides from Baylis-Hillman adducts. It participates in reactions with enaminophosphonates to form chiral adducts with high enantioselectivity and serves as a key electrophile in cyclization reactions for quinoline derivatives. Its utility lies in facilitating the construction of complex heterocyclic and phosphonate-containing structures.

Technology Process of Phenyl vinyl sulfone

There total 66 articles about Phenyl vinyl sulfone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2-chloroethyl phenyl sulfone (938-09-0) → PVS (5535-48-8)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 - 24 ℃; for 20h;

DOI:10.1021/jo00068a063

Reference yield: 99.0%

phenylthioethylene (1822-73-7) → PVS (5535-48-8)

Guidance literature:

With C₄H₉N₂O₉W; In methanol; water; at 20 ℃; for 4h; chemoselective reaction;

DOI:10.1016/j.tetlet.2011.12.105

Reference yield: 95.0%

2-(phenylsulfonyl)ethanol (20611-21-6) → PVS (5535-48-8)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1080/00397910008087440

upstream raw materials:

2-chloroethyl phenyl sulfone

2-(phenylsulfonyl)ethanol

triethylamine

phenylthioethylene

Downstream raw materials:

2-ethoxyethyl phenyl sulphone

2-(phenylsulfonyl)ethanol

(1,2-dibromo-ethyl)-phenyl sulfone

1-Aethylthio-2-chloraethylsulfon

Refernces

Asymmetric Michael reaction: novel efficient access to chiral β-ketophosphonates

10.1016/j.tetasy.2007.02.023

The research investigates the asymmetric Michael reaction to develop a method for synthesizing chiral b-ketophosphonates, which are valuable precursors for b-amino and b-hydroxy-phosphonates and have biological significance. The study focuses on using chiral b-enaminophosphonates derived from (S)-1-phenylethylamine and various electrophilic alkenes to achieve b,b-disubstituted ketophosphonates with high enantioselectivity and good yields. Key chemicals involved include the non-commercial b-ketophosphonate precursors 3a–3d, which were synthesized through a series of reactions involving hydrazones, Arbuzov reactions, and deprotection steps. The enaminophosphonates 4a–4d were then reacted with Michael acceptors such as phenylvinylsulfone and methyl acrylate. The study concludes that the asymmetric Michael reaction on acyclic enaminophosphonate compounds with non-substituted Michael acceptors is feasible, yielding chiral b-ketophosphonates with high enantiomeric excesses, similar to acyclic enaminoester derivatives. The introduction of dibenzyl- or diphenyl-phosphonate groups, however, decreased reactivity and enantioselectivity compared to diethylphosphonate groups. The absolute configurations of the adducts were determined using vibrational circular dichroism (VCD) due to challenges in obtaining single-crystal samples for X-ray analysis. Future work aims to extend this reaction to substituted Michael acceptors.

Synthesis of 3-substituted-4-hydroxyquinoline N-oxides from the Baylis-Hillman adducts of o-nitrobenzaldehydes

10.1016/S0040-4020(02)01518-1

The study focuses on the synthesis of 3-substituted-4-hydroxyquinoline N-oxides from Baylis–Hillman adducts derived from o-nitrobenzaldehydes. The key chemicals used in the study include trifluoroacetic acid, trifllic acid, and various Baylis–Hillman adducts such as 1b–f, which are derived from methyl vinyl ketone, phenyl vinyl sulfone, and ethyl acrylate. These chemicals serve the purpose of facilitating the reaction that yields the desired quinoline N-oxide derivatives. The study also explores the reaction mechanism, suggesting that N-hydroxyisoxazoline acts as a key intermediate in the process. The use of triflic acid was found to increase the acidity of the reaction medium, which was crucial for obtaining the quinoline N-oxides in reasonable yields. The study provides experimental evidence supporting the proposed reaction mechanism and successfully synthesizes several 3-substituted-4-hydroxyquinoline N-oxides, which are valuable synthetic intermediates.