13294-31-0

Usage

Uses

Used in Polymer and Resin Production:
[(Z)-2-ethoxyethenyl]benzene is used as a chemical intermediate for the manufacturing of polystyrene, a versatile plastic material. Polystyrene is widely utilized in the production of packaging materials, insulation, and a range of consumer goods due to its favorable properties such as clarity, rigidity, and resistance to water and electricity.
Used in Plastics and Elastomers:
Styrene oxide serves as a crosslinking agent in the production of various plastics and elastomers, enhancing their structural integrity, durability, and performance characteristics. This application is particularly relevant in industries where materials are subjected to mechanical stress or require increased resistance to environmental factors.
Used in Pharmaceutical and Agricultural Chemical Synthesis:
[(Z)-2-ethoxyethenyl]benzene is also employed as a key component in the synthesis of certain pharmaceuticals and agricultural chemicals, highlighting its versatility and importance in the chemical industry.
It is crucial to handle and use [(Z)-2-ethoxyethenyl]benzene with caution, as it is a toxic substance that can cause irritation to the skin, eyes, and respiratory system. Proper safety measures and guidelines should be followed to minimize potential health risks during its production and application.

Upstream product

• 64-17-5 ethanol 
• 536-74-3 phenylacetylene 
• 108-86-1 bromobenzene 
• 64724-29-4 tributyl-((Z)-2-ethoxy-vinyl)-stannane 
• 109-92-2 ethyl vinyl ether 
• 64-67-5 diethyl sulfate 
• 122-78-1 phenylacetaldehyde 

Downstream Products

• 278167-61-6 1-(p-toluenesulfonyl)-3-(p-methoxyphenyl)-4-phenyl-1H-pyrrole 
• 51832-29-2 3,4-diphenyl-1-tosyl-1H-pyrrole 
• 130146-89-3 (2S^*,3R^*,4S^*)-2-ethoxy-4-(ethoxycarbonyl)-3-phenyl-1-(phenylsulfonyl)-1,2,3,4-tetrahydropyridine 
• 130146-89-3 (2R^*,3S^*,4S^*)-2-ethoxy-4-(ethoxycarbonyl)-3-phenyl-1-(phenylsulfonyl)-1,2,3,4-tetrahydropyridine 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 100-52-7 benzaldehyde 
• 343941-51-5 2-ethoxy-2-methoxy-1-phenylethanol 

Relevant academic research and scientific papers

Base-promoted stereoselective hydroalkoxylation of alkynes

Base-promoted and stereoselective synthesis of C(sp2)-O bond through the anti-Markovnikov addition of alcohols onto alkyne and has been discovered. Developed protocol tolerates a wide variety of functional groups to afford styryl ethers from commercially

Interrogating Pd(II) Anion Metathesis Using a Bifunctional Chemical Probe: A Transmetalation Switch

Ligand metathesis of Pd(II) complexes is mechanistically essential for cross-coupling. We present a study of halide→OH anion metathesis of (Ar)PdII complexes using vinylBPin as a bifunctional chemical probe with Pd(II)-dependent cross-coupling pathways. We identify the variables that profoundly impact this event and allow control to be leveraged. This then allows control of cross-coupling pathways via promotion or inhibition of organoboron transmetalation, leading to either Suzuki-Miyaura or Mizoroki-Heck products. We show how this transmetalation switch can be used to synthetic gain in a cascade cross-coupling/Diels-Alder reaction, delivering borylated or non-borylated carbocycles, including steroid-like scaffolds.

Intermolecular Hydroalkoxylation of Terminal Alkynes Catalyzed by a Dipyrrinato Rhodium(I) Complex with Unusual Selectivity

An operationally simple and atom-economical method for the E-selective preparation of enol ethers is described. A novel dicarbonyl(5-phenyldipyrrinato)rhodium complex, 2, was prepared in four synthetic steps, characterized by X-ray crystallography and NMR

Rhodium-catalyzed anti-Markovnikov intermolecular hydroalkoxylation of terminal acetylenes

We report here the first transition-metal-catalyzed anti-Markovnikov intermolecular hydroalkoxylation of terminal acetylenes to give enol ethers in high yields without using bases. Arylacetylenes as well as alkenyl- and alkylacetylenes were coupled with aliphatic alcohols, and the products were obtained with high Z selectivity in most cases. Effective catalysts were 8-quinolinolato rhodium complexes, which are structurally simple but have been relatively unexplored as catalysts.

Synthesis of chiral acetals by asymmetric selenenylations

Asymmetric selenenylations of (E)-ethoxystyrene are described leading to chiral acetals. An efficient synthesis of such compounds including the determination of their absolute configuration is described.

Solvolysis of styryliodonium salt: Products, rates, and mechanisms

The solvolysis of phenyl[(E)-styryl]iodonium tetrafluoroborate in various solvents was examined at 50-70°C by means of product and kinetic studies with the normal and labeled substrates. The reactions involved are α-elimination and substitutions with configurational retention and inversion. In methanol and ethanol, the main reaction is α-elimination, along with about 5% of substitution with the ratio of inversion/retention from 4/6 to 3/7. As the basicity of the solvent decreases, the reaction rate and the fraction of α-elimination decrease, and at the same time the ratio of inversion/retention of substitution also decreases. In 2,2,2- trifluoroethanol, only the substitution with retention was observed. Labeling experiments showed that complete isotope scrambling occurred between the olefinic hydrogens of the retained product while the deuterium remained at the original position of the inverted product. The substitution mechanism is concluded to involve parallel pathways: an S(N) 1-type with a vinylenebenzenium ion intermediate leading to retention and a vinylic S(N) 2- type with a direct attack by the nucleophilic solvent leading to inversion.

Condensed heteroaromatic ring systems. XVII. Palladium-catalyzed cross-coupling reaction of aryl bromides with (Z)-1-ethoxy-2-tributylstannylethene and its utilization for construction of condensed heteroaromatics

The palladium-catalyzed cross-coupling reaction of bromobenzenes or bromoheteroarenes such as pyridine, thiophene, indole with (Z)-1-ethoxy-2-tributylstannylethene gives good yields of the corresponding (Z)-1-ethoxy-2-(aryl and heteroaryl)ethenes. This method is effective for introducing an ethoxyethenyl group into an aromatic and heteroaromatic ring and is proved to have versatile utility for the construction of benzo[b]furan, indole, isocoumarin rings 2-bromophenol, 2-bromoaniline, and 2-bromobenzoate derivatives.

REACTION OF ARYL HALIDES WITH (Z)-1-ETHOXY-2-TRIBUTYLSTANNYLETHENE: A VERSATILE METHOD FOR THE INTRODUCTION OF 2-ETHOXYETHENYL GROUP INTO AROMATIC NUCLEI

The reaction of 4-substituted bromobenzenes, except for 4-bromophenol and 4-bromoaniline, with (Z)-1-ethoxy-2-tributylstannylethene is well prompted by the catalytic action of dichlorobis(triphenylphosphine)palladium in dimethylformamide in the presence o