16619-62-8

Basic information

• Product Name: [(2-phenylethenyl)sulfinyl]benzene
• CAS NO: 16619-62-8
• Molecular Formula: C₁₄H₁₂OS
• Molecular Weight: 228.3095
• Mol File: 16619-62-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 440.2°C at 760 mmHg
• Flash Point: 220.1°C
• Density: 1.22g/cm³
• Vapor Pressure: 1.55E-07mmHg at 25°C
• Refractive Index: 1.665
• CAS DataBase Reference: [(2-phenylethenyl)sulfinyl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: [(2-phenylethenyl)sulfinyl]benzene(16619-62-8)
• EPA Substance Registry System: [(2-phenylethenyl)sulfinyl]benzene(16619-62-8)

Safety Data

• Hazardous Substances Data: 16619-62-8(Hazardous Substances Data)

Usage

Description

[(2-phenylethenyl)sulfinyl]benzene, also known as thioanethole, is a chemical compound characterized by its sulfurous aroma. It is a sulfide compound that consists of a benzene ring with a sulfinyl group and a phenylethenyl substituent. Thioanethole is commonly found in the essential oils of various plants, such as garlic, onion, and leek, and is responsible for the characteristic smell and flavor of these vegetables. It has been studied for its potential health benefits, including antioxidant and antimicrobial properties, but caution is advised as it may have toxic effects if ingested in large amounts. Thioanethole is an important compound in the food and pharmaceutical industries due to its aromatic and functional properties.

Uses

Used in Flavoring Agents:
[(2-phenylethenyl)sulfinyl]benzene is used as a flavoring agent in the food industry for its characteristic smell and flavor, which is derived from its presence in the essential oils of plants like garlic, onion, and leek.
Used in Pharmaceutical Applications:
[(2-phenylethenyl)sulfinyl]benzene is used as a compound with potential health benefits in the pharmaceutical industry, particularly for its antioxidant and antimicrobial properties. However, its use should be carefully monitored due to the potential toxic effects if ingested in large amounts.
Used in Essential Oils:
[(2-phenylethenyl)sulfinyl]benzene is used as a key component in the essential oils of various plants, contributing to their distinct aroma and flavor. This application is important in the fragrance and flavor industries, as well as in traditional medicine and aromatherapy.

Upstream product

• 1193-82-4 racemic methyl phenyl sulfoxide 
• 100-52-7 benzaldehyde 
• 50746-65-1 Diethyl (phenylsulfinyl)methylphosphonate 
• 16619-61-7 1-phenyl-2-phenylthioethene 
• 38066-16-9 diethyl [(phenylthio)methyl]phosphonate 
• 442160-22-7 1-acetoxy-1-phenyl-2-(phenylsulfinyl)ethane 

Downstream Products

• 219601-29-3 (3-Benzenesulfinyl-1,1-difluoro-2-phenyl-propyl)-phosphonic acid diethyl ester 
• 78429-05-7 3-phenyl4-phenylsulfinylbutanoic acid 

Relevant articles and documents

Palladium-Catalyzed Reductive [5+1] Cycloaddition of 3-Acetoxy-1,4-enynes with CO: Access to Phenols Enabled by Hydrosilanes

A new palladium-catalyzed reductive [5+1] cycloaddition of 3-acetoxy-1,4-enynes with CO, enabled by hydrosilanes, has been developed for delivering valuable functionalized phenols. This methodology employs hydrosilanes as the external reagent to facilitate the [5+1] carbonylative benzannulation. The reaction is a conceptually and mechanistically novel carbonylative cycloaddition route for the construction of substituted phenols, through the formation of four new chemical bonds, with excellent functional-group tolerance.

Synthesis of Sulfoxides by the Hydrogen Peroxide Induced Oxidation of Sulfides Catalyzed by Iron Tetrakis(pentafluorophenyl)porphyrin: Scope and Chemoselectivity

The oxidation of sulfides with H2O2 catalyzed by iron tetrakis(pentafluorophenyl)porphyrin in EtOH is an efficient and chemoselective process. With a catalyst concentration 0.03-0.09% of that of the substrate, sulfoxides are obtained with yields generally around 90-95% of isolated product. With vinyl and allyl sulfides, no epoxidation is observed. With a catalyst concentration between 0.09% and 0.25% of that of the substrate, sulfones are obtained in almost quantitative yield and with the same high chemoselectivity observed in the synthesis of sulfoxides.

A conjugate addition/sulfoxide elimination route to allylic difluorophosphonates

Cerium-mediated conjugate additions of (diethoxyphosphinoyl) difluoromethyllithium to cyclic vinyl sulfoxides proceeded smoothly; thermal sulfoxide elimination afforded the products of formal vinylation, attaching the difluoromethylenephosphonato group to an alkenyl carbon atom. With acyclic vinyl sulfoxides, the addition occurred in moderate to poor yield. Addition failed completely in the absence of cerium(III) chloride, and was facilitated by an excess of the reagent.