1918-82-7

Usage

Uses

Used in Polymer and Resin Production:
2-Vinylthiophene is used as a monomer in the production of polymers and resins, contributing to the development of materials with specific properties for various applications.
Used in Pharmaceutical and Agrochemical Synthesis:
2-Vinylthiophene serves as a starting material for the synthesis of various pharmaceuticals and agrochemical products, playing a crucial role in the development of new drugs and pesticides.
Used in Dye, Fragrance, and Flavoring Industries:
2-Vinylthiophene is utilized in the manufacture of dyes, fragrances, and flavorings, providing a wide range of color, scent, and taste options for different products.

Upstream product

• 5402-55-1 2-thiophenethanol 
• 75-01-4 chloroethylene 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 188290-36-0 thiophene 
• 123-63-7 paracetaldehyde 
• 115510-91-3 1-(thien-2-yl)ethanol 
• 4298-52-6 2-ethynyl-thiophene 
• 98-03-3 thiophene-2-carbaldehyde 
• 75-24-1 trimethylaluminum 
• 593-60-2 Vinyl bromide 
• 81745-84-8 2-thienylzinc chloride 
• 872-55-9 2-ethylthiophene 
• 28612-98-8 2-chloro-2-(2-thienyl)ethane 
• 1003-09-4 2-bromothiophene 

Downstream Products

• 4461-29-4 2-(thiophen-2-yl)acetamide 
• 53631-87-1 5,9a-dihydro-2-phenylthieno<3,2-c><1,2,4>triazolo<1,2-a>pyridazine-1,3-dione 
• 22390-25-6 Thieno<3,2-c>pyridazin 
• 91319-36-7 5,6-dihydro-2-phenyl-6-(3,5-dioxo-4-phenyl-1,2,4-triazolin-1-yl)thieno<3,2-c><1,2,4>triazolo<1,2-a>pyridazine-1,3-dione 
• 83927-06-4 dimethyl 2-(thiophen-2-yl)cyclopropane-1,1-dicarboxylate 
• 100590-43-0 methyl benzothiophen-4-carboxylate 
• 100590-44-1 dimethyl 7-(2-propenoato)-6,7-dihydrobenzothiophen-4-carboxylate 
• 101360-69-4 methyl 4,6-di(2-thienyl)cyclohex-1-en-1-carboxylate 
• 100590-45-2 dimethyl benzothiophen-4,7-dicarboxylate 
• 100590-40-7 dimethyl benzothiophen-4,5-dicarboxylate 
• 100590-41-8 dimethyl-3,5-di(2-thienyl)cyclohex-1-en-1,2-dicarboxylate 
• 100590-42-9 tetramethyl (E)-2-(2-butendionato)-6,7-dihydrobenzothiophen-4,5-dicarboxylate 
• 100590-42-9 tetramethyl (Z)-2-(2-butendionato)-6,7-dihydrobenzothiophen-4,5-dicarboxylate 
• 571-60-8 1,4-Dihydroxynaphthalene 

Relevant academic research and scientific papers

OXIDATIVE DEHYDROGENATION OF ALKYLHETEROAROMATIC COMPOUNDS. 2. DEHYDROGENATION OF ALKYLTHIOPHENES

The dehydrogenation of a series of alkylthiophenes has been studied on vanadium-magnesium systems in the presence of atmospheric oxygen, and zinc-chromium oxide catalysts in the absence of oxygen.Optimum conditions heve been determined for bringing this about enabling vinylthiophenes to be obtained in high yield and with high selectivity.The advantages of the oxidative dehydrogenation method have been shown in the synthesis of vinyl derivatives of thiophene.

Stereoselective Gold(I)-Catalyzed Vinylcyclopropanation via Generation of a Sulfur-Substituted Vinyl Carbene Equivalent

A stereoselective gold(I)-catalyzed vinylcyclopropanation of alkenes has been developed. A gold-coordinated cationic vinyl carbene species, readily generated via a rearrangement of the ethylenedithioacetal of propargyl aldehyde, reacts with a wide range of alkenes to afford thio-substituted vinylcyclopropanes. The gold-catalyzed vinyl cyclopropanation proceeds under mild conditions at room temperature and is generally selective for the formation of cis-substituted cyclopropanes. The reaction allows the formal introduction of a “naked” vinyl carbene, by subsequent chemoselective hydrodesulfurisation of the ethylenedithio-bridge. The synthetic utility of the new method is demonstrated by a short, racemic formal synthesis of the alkaloid cephalotaxin, hinging on a key vinyl cyclopropane-cyclopentene rearrangement.

Tertiary arsine ligands for the Stille coupling reaction

The Stille coupling reaction is one of the most important coupling reactions. It is well known that the triphenylarsine ligand can accelerate the reaction rate of Stille coupling. However, other arsine ligands have never been investigated for the Stille c

Selective Transfer Semihydrogenation of Alkynes with H2O (D2O) as the H (D) Source over a Pd-P Cathode

We reported a selective semihydrogenation (deuteration) of numerous terminal and internal alkynes using H2O (D2O) as the H (D) source over a Pd-P alloy cathode at a lower potential. P-doping caused the enhanced specific adsorption of alkynes and the promoted intrinsic activity for producing adsorbed atomic hydrogen (H*ads) from water electrolysis. The semihydrogenation of alkynes could be accomplished at a lower potential with up to 99 % selectivity and 78 % Faraday efficiency of alkene products, outperforming pure Pd and commercial Pd/C. This electrochemical semihydrogenation of alkynes might proceed via a H*ads addition pathway rather than a proton-coupled electron transfer process. The decreased amount of H*ads at a lower potential and the more preferential adsorption of the Pd-P to C≡C π bond than C=C moiety resulted in the excellent alkene selectivity. This method was capable of producing mono-, di-, and tri-deuterated alkenes with up to 99 % deuterium incorporation.

Iron-Catalyzed Direct Julia-Type Olefination of Alcohols

Herein, we report an iron-catalyzed, convenient, and expedient strategy for the synthesis of styrene and naphthalene derivatives with the liberation of dihydrogen. The use of a catalyst derived from an earth-abundant metal provides a sustainable strategy to olefins. This method exhibits wide substrate scope (primary and secondary alcohols) functional group tolerance (amino, nitro, halo, alkoxy, thiomethoxy, and S- A nd N-heterocyclic compounds) that can be scaled up. The unprecedented synthesis of 1-methyl naphthalenes proceeds via tandem methenylation/double dehydrogenation. Mechanistic study shows that the cleavage of the C-H bond of alcohol is the rate-determining step.

Hydrazide-Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of cis-Decalins

Polyene cyclizations offer rapid entry into terpenoid ring systems. Although enantioselective cyclizations of (E)-polyenes to form trans-decalin ring systems are well precedented, highly enantioselective cyclizations of (Z)-polyenes to form the correspond

Biocatalytic asymmetric ring-opening of dihydroisoxazoles: a cyanide-free route to complementary enantiomers of β-hydroxy nitriles from olefins

By combination of the cyanide-free synthesis of chiral nitriles and the Kemp elimination reaction catalyzed by aldoxime dehydratases, we herein report a new application of aldoxime dehydratase in the asymmetric ring-opening of 5-sub-4,5-dihydroisoxazoles

Br?nsted Acid Catalyzed Peterson Olefinations

A mild and facile Peterson olefination has been developed employing low catalyst loading of the Br?nsted acid HNTf2. The reactions are typically performed at room temperature, with the reaction tolerant to a range of useful functionalities. Furthermore, we have extended this methodology to the synthesis of enynes.

Efficient and Practical Transfer Hydrogenation of Ketones Catalyzed by a Simple Bidentate Mn?NHC Complex

Catalytic reductions of carbonyl-containing compounds are highly important for the safe, sustainable, and economical production of alcohols. Herein, we report on the efficient transfer hydrogenation of ketones catalyzed by a highly potent Mn(I)?NHC complex. Mn?NHC 1 is practical at metal concentrations as low as 75 ppm, thus approaching loadings more conventionally reserved for noble metal based systems. With these low Mn concentrations, catalyst deactivation is found to be highly temperature dependent and becomes especially prominent at increased reaction temperature. Ultimately, understanding of deactivation pathways could help close the activity/stability-gap with Ru and Ir catalysts towards the practical implementation of sustainable earth-abundant Mn-complexes.

Additive-modulated switchable reaction pathway in the addition of alkynes with organosilanes catalyzed by supported Pd nanoparticles: Hydrosilylation: versus semihydrogenation

We herein report supported Pd nanoparticles on N,O-doped hierarchical porous carbon as a single operation catalyst-enabled additive-modulated reaction pathway for alkynes addition with organosilanes between hydrosilyation and semihydrogenation. In the case of alkynes hydrosilylation, a simple iodide ion as an additive has a promotion effect on the activity and regio- and stereoselectivity, where iodide can coordinate with Pd NPs via strong δ donation to increase the electron density of the Pd atom, resulting in an increased ability for the oxidative addition of hydrosilane as the rate-determining step to make the reaction proceed efficiently to afford vinylsilanes in high yields with excellent regio- and stereoselectivity. For the catalytic transfer semihydrogenation of alkynes, water was introduced to mix with organosilane to form a silanol together with the generation of hydrogen atoms on the Pd NPs surface or the liberation of H2 gas as a reducing agent, whereby the quantitative reduction of alkynes was achieved with exclusive selectivity to alkenes. In both cases, the catalyst could be recycled several times without a significant loss in activity or selectivity. A broad range of alkyl and aryl alkynes with various functional groups are compatible with the reaction conditions. The role the additive exerted in each reaction was extensively investigated through control experiments as well as the kinetic isotopic effect along with spectroscopic characterization. In addition, the respective mechanism operating in both reactions was proposed.