Thiophene, 3-(2-phenylethenyl)-

Base Information

• Chemical Name: Thiophene, 3-(2-phenylethenyl)-
• CAS No.: 35022-11-8
• Molecular Formula: C12H10S
• Molecular Weight: 186.277
• Mol file: 35022-11-8.mol

Synonyms:

Chemical Property of Thiophene, 3-(2-phenylethenyl)-

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Thiophene, 3-(2-phenylethenyl)-

There total 7 articles about Thiophene, 3-(2-phenylethenyl)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3-Bromothiophene (872-31-1) + styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) → 3-styryl-thiophene (35022-11-8)

Guidance literature:

With C₅₀H₆₄Cl₂N₁₂Pd₂⁽⁶⁺⁾*6F₆P^(1-); sodium acetate; In N,N-dimethyl-formamide; at 140 ℃; for 4h; Reagent/catalyst;

DOI:10.1016/j.jorganchem.2012.11.015

Reference yield: 54.0%

3-[(phenylsulfonyl)methyl]thiophene (129759-54-2) + benzyl alcohol (100-51-6,185532-71-2) → 3-styryl-thiophene (35022-11-8)

Guidance literature:

With potassium tert-butylate; C₂₃H₁₉N₃O₂S; nickel dibromide; In toluene; at 140 ℃; for 48h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00545

Reference yield:

3-ethynylthiophene (67237-53-0) + sodium tetraphenyl borate (143-66-8) → 3-styryl-thiophene (35022-11-8) + C18H14S2

Guidance literature:

With bis(3-N-benzylimidazole)dichloropalladium(II); acetic acid; In water; at 20 ℃; for 3h; Schlenk technique;

DOI:10.1016/j.apcata.2019.117243

upstream raw materials:

3-thiophene carboxaldehyde

O,O-diethyl benzylphosphonate

(thiophene-3-ylmethyl)phosphonic acid diethyl ester

benzaldehyde

Downstream raw materials:

naphtho[1,2-b]thiophene

3-thiophene carboxaldehyde

benzaldehyde

[2,2']Bi[naphtho[1,2-b]thiophenyl]

Refernces

Photocyclization and photooxidation of 3-styrylthiophene

10.1016/S0040-4039(00)00097-6

The study focuses on the photocyclization and photooxidation processes of 3-styrylthiophene, a compound with two isomers: trans-3-styrylthiophene (1) and cis-3-styrylthiophene (2). The research investigates how these isomers react under different photochemical conditions, including in nonpolar and polar solvents, with and without sensitizers. The key findings include that cis-3-styrylthiophene (2) undergoes photochemical cis–trans isomerization and cyclization to form dihydronaphtho-[1,2-b]thiophene (3), with a higher quantum efficiency in nonpolar solvents. Dye-sensitized photooxidation of 3-styrylthiophene results in the production of benzaldehyde and 3-thiophenecarboxaldehyde, and the process is suggested to occur via a superoxide radical anion pathway rather than through singlet oxygen. Additionally, auto-photooxidation in the presence of oxygen leads to photocyclization, oxidation, and dimerization products. The study proposes that these reactions may involve the formation of a charge transfer complex between oxygen and the substrate. The research is significant for understanding the behavior of polythiophenes, which are important for the production of conductive polymers, and could contribute to improving the photostability of these materials.

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