24182-83-0

Basic information

• Product Name: 1-methyl-4-{[(Z)-2-phenylethenyl]sulfanyl}benzene
• CAS NO: 24182-83-0
• Molecular Formula: C₁₅H₁₄S
• Molecular Weight: 226.3367
• Mol File: 24182-83-0.mol

Chemical Properties

• Boiling Point: 362.3°C at 760 mmHg
• Flash Point: 168°C
• Density: 1.09g/cm³
• Vapor Pressure: 4.07E-05mmHg at 25°C
• Refractive Index: 1.627
• CAS DataBase Reference: 1-methyl-4-{[(Z)-2-phenylethenyl]sulfanyl}benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-4-{[(Z)-2-phenylethenyl]sulfanyl}benzene(24182-83-0)
• EPA Substance Registry System: 1-methyl-4-{[(Z)-2-phenylethenyl]sulfanyl}benzene(24182-83-0)

Safety Data

• Hazardous Substances Data: 24182-83-0(Hazardous Substances Data)

Usage

Physical state

colorless liquid
Thioanisole is a colorless liquid, meaning it does not have any color and flows like a liquid at room temperature.

Odor

sweet, aromatic
Thioanisole has a sweet and aromatic odor, which contributes to its use as a flavor and fragrance ingredient.

Common uses

flavor and fragrance ingredient, solvent, synthesis of organic compounds, and reagent in organic chemistry reactions
Thioanisole is commonly used in various applications, such as a flavor and fragrance ingredient in perfumes, dyes, and pharmaceuticals, as a solvent, in the synthesis of organic compounds, and as a reagent in organic chemistry reactions.

Hazardous properties

flammable, potentially hazardous
Thioanisole is a flammable and potentially hazardous substance, which means it should be handled with care to avoid accidents and ensure safety.

Upstream product

• 10486-08-5 sodium p-thiocresolate 
• 536-74-3 phenylacetylene 
• 141-52-6 sodium ethanolate 
• 106-45-6 para-thiocresol 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 933-00-6 p-methylbenzenesulfenyl chloride 
• 42599-24-6 E-styryl iodide 
• 100-42-5 styrene 
• 934-72-5 Methyl p-tolyl sulfoxide 
• 63707-12-0 1-(4-methylphenylsulfanyl)-2-phenylethyne 
• 38986-89-9 trans-cinnamoyl fluoride 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 2757-04-2 phenyl cinnamate 
• 2943-42-2 di(4-methyl)phenylthiosulfonate 

Downstream Products

• 479623-83-1 (+/-)-(Z)-5-phenyl-4-(p-tolylsulfenyl)pent-4-en-3-ol 
• 1068599-48-3 CH₃C₆H₄SCHCH₂C₆H₅BO₂C₆H₄ 
• 156575-60-9 2-(1-phenyl-ethyl)-benzo[1,3,2]dioxaborole 
• 1068599-50-7 CH₃C₆H₄SCH₂CHBO₂C₆H₄C₆H₅ 
• 156575-59-6 2-(2-phenylethyl)benzo-1,3,2-dioxaborole 
• 174090-36-9 4,4,5,5-tetramethyl-2-(1-phenyl-ethyl)-[1,3,2]dioxaborolane 
• 165904-22-3 4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane 
• 19062-76-1 (1-phenyl-2-tosylethyl)-(p-tolyl)sulfane 
• 211929-53-2 (2-tosylethane-1,1-diyl)dibenzene 
• 19719-87-0 1-methyl-4-(phenethylsulfonyl)benzene 
• 2779-69-3 1,1-dichloro-2,2-diphenylethene 

Relevant articles and documents

Base-Promoted Stereoselective Hydrogenation of Ynamides with Sulfonyl Hydrazide to Give Z-Enamides

A base-mediated semihydrogenation of ynamides using p-toluenesulfonyl hydrazide as an inexpensive and easy-to-handle hydrogen donor is reported. This transition-metal-free protocol avoids overhydrogenation and reduction of other functional groups, generating the thermodynamically unfavorable Z-enamides exclusively.

Transition Metal-Free C-H Thiolation via Sulfonium Salts Using β-Sulfinylesters as the Sulfur Source

We disclose a direct C(sp)-, C(sp2)-, and C(sp3)-H thiolation reaction using β-sulfinylesters as the versatile sulfur source. The key step of this protocol is chemoselective C-S bond cleavage of the sulfonium salts that are formed in situ from the corresponding alkenes, alkynes, and 1,3-dicarboxyl compounds with β-sulfinylesters. The successful capture of the acrylate byproduct supports a retro-Michael reaction mechanism.

Nickel-Catalyzed Decarbonylative Thioetherification of Acyl Fluorides via C-F Bond Activation

Nickel-catalyzed decarbonylative thioetherification of acyl fluorides has been developed. This transformation allows an array of acyl fluorides to react with thiophenols. A wide range of functional groups are well tolerated and the corresponding sulfides can be obtained in good to excellent yields. This protocol provides the formation of diverse carbon-sulfur bonds via a highly efficient decarbonylative process.

Electrophilic Vinylation of Thiols under Mild and Transition Metal-Free Conditions

The iodine(III) reagents vinylbenziodoxolones (VBX) were employed to vinylate a series of aliphatic and aromatic thiols, providing E-alkenyl sulfides with complete chemo- and regioselectivity, as well as excellent stereoselectivity. The methodology displays high functional group tolerance and proceeds under mild and transition metal-free conditions without the need for excess substrate or reagents. Mercaptothiazoles could be vinylated under modified conditions, resulting in opposite stereoselectivity compared to previous reactions with vinyliodonium salts. Novel VBX reagents with substituted benziodoxolone cores were prepared, and improved reactivity was discovered with a dimethyl-substituted core.

Anti-Markovnikov stereoselective hydroamination and hydrothiolation of (hetero)aromatic alkynes using a metal-free cyclic trimeric phosphazene base

Hydroamination and hydrothiolation are the most efficient and completely atom-economical process to construct important enamine and vinyl sulfide intermediates in pharmaceutical and organic chemistry. The cyclic trimeric phosphazene base (CTPB) showed gre

Zinc-Catalyzed Synthesis of Dithioacetals through Double Hydrosulfenylation of Alkynes by Thiols

Zinc-catalyzed hydrosulfenylation of alkenes can be performed in various solvents, and the corresponding products are obtained regioselectively. Dihydrosulfenylation of alkynes with thiols can also be achieved by using a zinc catalyst, and the reaction is preferentially promoted over monohydrosulfenylation. The reaction can also give dithioacetals regioselectively in excellent yields.

Nickel-Catalyzed C?S Bond Formation via Decarbonylative Thioetherification of Esters, Amides and Intramolecular Recombination Fragment Coupling of Thioesters

A nickel catalyzed cross-coupling protocol for the straightforward C?S bond formation has been developed. Various mercaptans and a wide range of ester and amide substrates bearing various substituents were tolerated in this process which afforded products in good to excellent yields. Furthermore, an intramolecular protocol for the synthesis of thioethers starting from thioesters has been developed. The utility of this protocol has been demonstrated in a new synthetic protocol of benzothiophene.

Modified conditions for copper-catalyzed ipso-thiolation of arylboronic acid esters with thiosulfonates

An efficient ipso-thiolation of arylboronic acid esters with thiosulfonates has been achieved under mild and odorless conditions using a copper catalyst. The use of TMEDA and cesium fluoride as the ligand and base, respectively, dramatically facilitated the desired transformation. The method exhibited a broad substrate scope, which allowed for the expeditious synthesis of diverse aryl sulfides from easily available starting materials.

Regioselective hydrothiolation of terminal acetylene catalyzed by magnetite (Fe3O4) nanoparticles

Herein, we report a new and solvent-free methodology for the preparation of vinyl thioethers from terminal alkynes and thiols, using magnetite (Fe3O4) nanoparticles as a recyclable catalyst. With this greener method, the desired viny

Stereoselective Synthesis of Alkenyl Silanes, Sulfones, Phosphine Oxides, and Nitroolefins by Radical C-S Bond Cleavage of Arylalkenyl Sulfides

A radical-mediated approach has been introduced for the C-S bond activation of arylalkenyl sulfides. The protocol provides an efficient approach for the generation of various alkenes including alkenyl silanes, sulfones, phosphine oxides, and nitroolefins. In most cases, these radical substitutions are performed under metal-free conditions with stereospecificity.