1822-73-7

Basic information

• Product Name: PHENYL VINYL SULFIDE
• Synonyms: Phenyl Vinyl Sulfide (stabilized with TBC);phenyl(vinyl)sulfane;(Ethenylthio)benzene;Ethenyl phenyl sulfide;Phenyl vinyl sulfide,97%;ethenylsulfanylbenzene;(Vinylsulfanyl)benzene;Benzene,(ethenylthio)-
• CAS NO: 1822-73-7
• Molecular Formula: C₈H₈S
• Molecular Weight: 136.21
• EINECS: 217-351-2
• Product Categories: Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfides/Disulfides;Sulfur Compounds
• Mol File: 1822-73-7.mol

Chemical Properties

• Boiling Point: 94-95 °C25 mm Hg(lit.)
• Flash Point: 114 °F
• Appearance: clear slightly yellowish liquid
• Density: 1.042 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.492mmHg at 25°C
• Refractive Index: n20/D 1.599(lit.)
• Storage Temp.: 2-8°C
• BRN: 969970
• CAS DataBase Reference: PHENYL VINYL SULFIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYL VINYL SULFIDE(1822-73-7)
• EPA Substance Registry System: PHENYL VINYL SULFIDE(1822-73-7)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 13
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 1822-73-7(Hazardous Substances Data)

Usage

Chemical Description

Phenyl vinyl sulfide and aryl nitrile oxides are starting materials for the reaction, and the isoxazoline compounds are intermediates in the synthesis of the b-enamino thioesters.

Uses

Used in Chemical Synthesis:
PHENYL VINYL SULFIDE is used as a chemical intermediate for the synthesis of 2-fluoropyridinyl-6-oxyprecursors. Its unique chemical structure allows it to serve as a crucial component in the creation of these precursors, which can be further utilized in the development of various pharmaceuticals and other chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, PHENYL VINYL SULFIDE is used as a key component in the development of new drugs and medications. Its role in the synthesis of important precursors makes it a valuable asset in the ongoing research and development of novel pharmaceutical compounds.
Used in Chemical Research:
PHENYL VINYL SULFIDE is also used in chemical research as a versatile compound for exploring new reactions and understanding the behavior of different chemical groups. Its clear, slightly yellowish liquid form makes it easy to handle and manipulate in laboratory settings, contributing to the advancement of chemical knowledge and innovation.

Synthesis Reference(s)

Journal of the American Chemical Society, 81, p. 2146, 1959 DOI: 10.1021/ja01518a032Synthesis, p. 577, 1978Tetrahedron Letters, 33, p. 199, 1992 DOI: 10.1016/0040-4039(92)88049-B

InChI:InChI=1/C8H8S/c1-2-9-8-6-4-3-5-7-8/h2-7H,1H2

Upstream product

• 69582-37-2 bicyclo[2.2.1]hept-5-en-2-yl(phenyl)sulfane 
• 622-20-8 1,2-bis(phenylthio)ethane 
• 63196-76-9 2-Phenylthiocyclopropylcarbonsaeuremethylester 
• 13307-56-7 1,1-bis(phenylthio)ethane 

Downstream Products

• 69582-37-2 bicyclo[2.2.1]hept-5-en-2-yl(phenyl)sulfane 
• 622-20-8 1,2-bis(phenylthio)ethane 
• 63196-76-9 2-Phenylthiocyclopropylcarbonsaeuremethylester 
• 13307-56-7 1,1-bis(phenylthio)ethane 

Relevant articles and documents

Highly efficient atom economical "green chemistry" synthesis of vinyl sulfides from thiols and acetylene in water

Potassium thiolates generated by treatment of thiols with aqueous KOH react with acetylene to give the corresponding vinyl sulfides in 90-95% yields.

Development of a highly efficient catalytic method for synthesis of vinyl ethers

A new method for the preparation of alkyl vinyl ethers has been developed. Thus, various types of alkyl vinyl ethers were synthesized by the reaction of alcohols with vinyl acetate under the influence of a catalytic amount of [Ir(cod)Cl]2 combined with Na2CO3 in good to excellent yields. Copyright

A NaX zeolite framework containing magnetic MgFe2O4/CdO nanoparticles: Synthesis, characterization and catalytic performance in the decontamination of 2-chloroethyl phenyl sulfide (2-CEPS) as a model of sulfur mustard agent

The present study highlights the successful fabrication of a zeolite NaX/MgFe2O4/CdO magnetically separable nanocomposite catalyst via an ultrasonic-assisted hydrothermal strategy for the decontamination of sulfur mustard agent simulant 2-chloroethyl phenyl sulfide (2-CEPS) for the first time. The as-fabricated nanocomposite was fully characterized using FESEM, TEM, EDAX, FTIR spectroscopy, XRD, AFM, VSM, N2-BET, and ICP-AES analyses. The decontamination process of 2-CEPS was monitored via GC-FID analysis. Furthermore, the effects of different analytical parameters such as contact time, catalyst type, catalyst amount and solvent type on the decontamination efficiency of 2-CEPS were precisely investigated. By using 50 mg of NaX/MgFe2O4/CdO catalyst in the presence of an n-heptane non-polar solvent, a decontamination efficiency of 100% was achieved after a contact time of 120 min. The decontamination process rate was verified by a first-order kinetic model. The obtained outcomes demonstrated that the apparent rate constant (kapp) and half-life time (t1/2) were 0.219 min-1 and 31.64 min, respectively. Lastly, the presence of hydrolysis and elimination products, namely 2-hydroxy ethyl phenyl sulfide (2-HEPS) and phenyl vinyl sulfide (PVS), from the effective degradation of 2-CEPS over the NaX/MgFe2O4/CdO catalyst was confirmed, and GC-MS analysis was performed to identify the degradation products of this agent simulant. This illustrates that the NaX/MgFe2O4/CdO catalyst could potentially be utilized for the removal of hazardous chemical warfare agents. This journal is

Electrophilic Chlorine from Chlorosulfonium Salts: A Highly Chemoselective Reduction of Sulfoxides

Herein, we describe a selective late-stage deoxygenation of sulfoxides based on a novel application of chlorosulfonium salts and demonstrate a new process using these species generated in situ from sulfoxides as the source of electrophilic chlorine. The use of highly nucleophilic 1,3,5-trimethoxybenzene (TMB) as the reducing agent is described for the first time and applied in the deoxygenation of simple and functionalized sulfoxides. The method is easy to handle, economic, suitable for gram-scale operations, and readily applied for poly-functionalized molecules, as demonstrated with more than 45 examples, including commercial medicines and analogues. We also report the results of competition experiments that define the more reactive sulfoxide and we present a mechanistic proposal based on substrate and product observations.

Efficient hydrodeoxygenation of sulfoxides into sulfides under mild conditions using heterogeneous cobalt-molybdenum catalysts

Nitrogen-doped carbon-supported cobalt-molybdenum bimetallic catalysts (abbreviated as Co-Mo/NC) are active for the hydrodeoxygenation of sulfoxides to sulfides under mild conditions (25-80 °C and 10 bar H2), which represents the first example of the use of heterogeneous non-noble metal catalysts for this transformation. MoO3 with Lewis acid sites assists the hydrodeoxygenation of sulfoxides into sulfides by hydrogen over cobalt nanoparticles.

Synthesis and characterization of TiO2/Mg(OH)2composites for catalytic degradation of CWA surrogates

Surface catalyzed reactions can be a convenient way to deactivate toxic chemical warfare agents (CWAs) and remove them from the contaminated environment. In this study, pure titanium oxide, magnesium hydroxide, and their composites TiO2/Mg(OH2) were prepared by thermal decomposition and precipitation of the titanium peroxo-complex and/or magnesium nitrate in an aqueous solution. The as-prepared composites were examined by XRD, XPS, HRTEM, and nitrogen physisorption. Their decontamination ability was tested on CWA surrogates and determined by high-performance liquid chromatography (HPLC) and gas chromatography coupled with mass spectrometry (GC-MS). Dimethyl methyl phosphonate (DMMP) was used as a G simulant for the nerve agents sarin (GB) and soman (GD) while 2-chloroethyl ethyl sulfide (2-CEES) and 2-chloroethyl phenyl sulfide (2-CEPS) were used as surrogates of sulfur mustard (HD). The activity of the as-prepared composites was correlated with acid-base properties determined by potentiometric titrations and pyridine adsorption studied byin situDRIFTS. The mixing of Ti and Mg led to an increase of the surface area and the amount of surface -OH groups (with an increasing amount of Ti) that caused improved degradation of DMMP.

Extended Pummerer fragmentation mediated by carbon dioxide and cyanide

Pummerer rearrangement reactions generate sulfur (II) oxidation state from sulfur (IV) starting materials in the presence of activating reagents. We found unprecedented transformation of vinyl sulfoxide; disulfide formation reactions mediated by atmospheric pressure of carbon dioxide in extended Pummerer rearrangement reactions. Only under CO2 atmosphere, we observed moderate to high yields of disulfide starting from sulfur (IV) starting materials. Investigations on the reaction mechanism revealed that the degradation of the starting materials and the products was significant in the absence of CO2. Further evidence for the suggested reaction mechanism was obtained by a cross-over experiment and a radical trapping reagent.

A Manganese N-Heterocyclic Carbene Catalyst for Reduction of Sulfoxides with Silanes

The first reduction of sulfoxides catalysed by a well-defined manganese complex is described. A variety of sulfoxides are reduced to the corresponding sulfides in high yields using phenylsilane, diphenylsilane, and the economically feasible 1,1,3,3-tetramethyldisiloxane (TMDS) as reducing agents in the presence of a Mn-NHC complex. The reaction is performed under air and without the need of any additive. The involvement of radicals in the catalytic reaction is probed by spin-trap experiments.

Safe and Metal-Free Synthesis of 1-Alkenyl Aryl Sulfides and Their Sulfones from Thiiranes and Diaryliodonium Salts

A series of 1-alkenyl aryl sulfides was synthesized from thiiranes and diaryliodonium salts in tetrahydrofuran in the presence of potassium tert -butoxide. The proposed reaction mechanism involves generation of benzynes from the diaryliodonium salts in the presence of the base. Then, nucleophilic attack of the benzynes by thiiranes, followed by hydrogen abstraction and ring opening of the generated thiiranium intermediates, provides the sulfides. These sulfides were further oxidized with performic acid to the corresponding sulfones. The current method provides a metal-free and safe method for the preparation of 1-alkenyl aryl sulfides and their sulfones.

Radical Hydroarylation of Functionalized Olefins and Mechanistic Investigation of Photocatalytic Pyridyl Radical Reactions

We report the photoredox alkylation of halopyridines using functionalized alkene and alkyne building blocks. Selective single-electron reduction of the halogenated pyridines provides the corresponding heteroaryl radicals, which undergo anti-Markovnikov addition to the alkene substrates. The system is shown to be mild and tolerant of a variety of alkene and alkyne subtypes. A combination of computational and experimental studies support a mechanism involving proton-coupled electron transfer followed by medium-dependent alkene addition and rapid hydrogen atom transfer mediated by a polarity-reversal catalyst.