3,4-Ethylenedioxythiophene

Base Information

• Chemical Name: 3,4-Ethylenedioxythiophene
• CAS No.: 126213-50-1
• Molecular Formula: C6H6O2S
• Molecular Weight: 142.178
• Hs Code.: 29349990
• Mol file: 126213-50-1.mol

Synonyms:2,3-Dihydrothieno[3,4-b]-1,4-dioxin;3,4-Ethyleneoxythiophene;EDOT;3,4-Ethylenedioxythiophene(EDOT);

Chemical Property of 3,4-Ethylenedioxythiophene

Chemical Property:

• Appearance/Colour: near colorless to pale yellow liquid with slightly unpleasant ordr
• Vapor Pressure: 0.278mmHg at 25°C
• Melting Point: 10 °C
• Refractive Index: n20/D 1.5765(lit.)
• Boiling Point: 210.494 °C at 760 mmHg
• Flash Point: 81.104 °C
• PSA: 46.70000
• Density: 1.319 g/cm³
• LogP: 1.51930
• Storage Temp.: 2-8°C
• Water Solubility.: Immsicible with water. Miscible with alcohol and ether.

Purity/Quality:

99.7% min (GC) ^*data from raw suppliers

3,4-Ethylenedioxythiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 21/22-36
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: 3,4-Ethylenedioxythiophene is used as a monomer to synthesize the conductive polymers and used as a reductant in the one-pot synthesis of gold nanoparticles from chloroauric acid, as starting material used in palladium-catalyzed mono and bis-arylation reactions and in the synthesis of conjugated polymers and copolymers, with potential optical applications. It is also used in redox activity, electroactivity and conductivity.

Technology Process of 3,4-Ethylenedioxythiophene

There total 24 articles about 3,4-Ethylenedioxythiophene 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: 98.0%

3,4-ethylenedioxythiophene-2,5-dicarboxyllic acid (18361-03-0) → 3,4-(ethylenedioxy)thiophene (126213-50-1)

Guidance literature:

copper; In ethylene glycol; at 20 - 140 ℃; for 8.5h;

Reference yield: 97.9%

2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid diethyl ester (154934-13-1) → 3,4-(ethylenedioxy)thiophene (126213-50-1)

Guidance literature:

With copper(II) oxide; zinc(II) oxide; In water; N,N-dimethyl-formamide; at 115 ℃; for 3h; Temperature; Catalytic behavior;

Reference yield: 84.0%

2,3-dimethoxythiophene (51792-34-8) + ethylene glycol (107-21-1) → 3,4-(ethylenedioxy)thiophene (126213-50-1)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 95 ℃; for 96h; Inert atmosphere;

DOI:10.1002/pola.25971

upstream raw materials:

3,4-ethylenedioxythiophene-2,5-dicarboxyllic acid

2,3-dimethoxythiophene

ethylene glycol

2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid diethyl ester

Downstream raw materials:

2,3-dihydro-7-(4-methoxyphenyl)thieno[3,4-b][1,4]dioxine-5-carbaldehyde

2,3-dihydro-7-p-tolylthieno[3,4-b][1,4]dioxine-5-carbaldehyde

tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-stannane

5-(p-tolyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine

Refernces

• 1、 Zhang, Hua,Qian, Chao,Chen, Xin-Zhi. "An improved procedure for the synthesis of 3,4-ethylenedioxythiophene". . p. 339 - 340. Retrieved 2011.
• 2、 Hachiya, Iwao,Yamamoto, Toshihiro,Inagaki, Tatsuhiko,Matsumoto, Tomohiro,Takahashi, Atsushi,Mizota, Isao,Shimizu, Makoto. "Two-step synthesis of 3,4-ethylenedioxythiophene (EDOT) from 2,3-butanedione". . p. 607 - 612. Retrieved 2014.
• 3、 Agrawal, Abhijeet R.,Kumar, Neha Rani,Debnath, Sashi,Das, Sarasija,Kumar, Chandan,Zade, Sanjio S.. "Radical-Cascade Avenue for 3,4-Fused-Ring-Substituted Thiophenes". . p. 4728 - 4731. Retrieved 2018.
• 4、 -. "Decarboxylation method of thieno[3,4-b]-1,4-dioxa-5,7-dicarboxylic acid". Paragraph 0023; 0024; 0025. . Retrieved 2017/02/28.