6297-65-0

Basic information

• Product Name: ethyl 3-oxo-3-phenyl-2-(phenylsulfonyl)propanoate
• CAS NO: 6297-65-0
• Molecular Formula: C₁₇H₁₆O₅S
• Molecular Weight: 332.3709
• Mol File: 6297-65-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 517.6°C at 760 mmHg
• Flash Point: 266.8°C
• Density: 1.275g/cm³
• Vapor Pressure: 8.07E-11mmHg at 25°C
• Refractive Index: 1.569
• CAS DataBase Reference: ethyl 3-oxo-3-phenyl-2-(phenylsulfonyl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-oxo-3-phenyl-2-(phenylsulfonyl)propanoate(6297-65-0)
• EPA Substance Registry System: ethyl 3-oxo-3-phenyl-2-(phenylsulfonyl)propanoate(6297-65-0)

Safety Data

• Hazardous Substances Data: 6297-65-0(Hazardous Substances Data)

Upstream product

• 873-55-2 sodium benzenesulfonate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 34320-89-3 2-iodo-3-oxo-3-phenyl-propionic acid ethyl ester 
• 55919-47-6 ethyl 2-bromo-3-oxo-3-phenylpropionate 

Relevant articles and documents

Switching of Sulfonylation Selectivity by Nature of Solvent and Temperature: The Reaction of β-Dicarbonyl Compounds with Sodium Sulfinates under the Action of Iron-Based Oxidants

Selectivity of sulfonylation of β-keto esters with sodium sulfinates under the action of iron(III) salts as oxidants can be regulated by the type of solvent used and the reaction temperature. α-Sulfonyl β-keto esters are obtained when the process is conducted in THF/H2O solution at 40 °C. The change of the solvent to iPrOH/H2O and refluxing of a reaction mixture provides α-sulfonyl esters – the products of successive sulfonylation-deacylation. When β-diketones are applied as starting materials, only α-sulfonyl ketones are formed. The reaction pathway includes sulfonylation of dicabonyl compounds under the action of Fe(III) to form α-sulfonylated dicarbonyl compounds, which are then attacked by a solvent as the nucleophile, resulting in the products of successive sulfonylation-deacylation. Participation of the solvent in the reaction pathway determines the products structure.

Metal-free desulfonylation reaction through visible-light photoredox catalysis

The desulfonylation of β-arylketosulfones has been achieved in good to excellent yields by using 3-W blue LEDs light, 1 mol-% organic dye eosin Y bis(tetrabutylammonium salt) as photocatalyst, and diisopropylethylamine as reducing agent. Mechanistic studies demonstrate that oxidative quenching of the excited eosin Y by β-arylketosulfones plays a crucial role in the present photoredox catalytic cycle. Reductive desulfonylation is essential to enable to use of a sulfone as an auxiliary group. For reductive removal of sulfones, highly aggressive metal-containing reducing agents and harsh reaction conditions are often employed. In this paper, metal-free desulfonylation of β-arylketosulfones can be achieved efficiently at room temperature under visible-light irradiation.