Diethyl 3,4-dihydroxythiophene-2,5-dicarboxylate

Base Information

• Chemical Name: Diethyl 3,4-dihydroxythiophene-2,5-dicarboxylate
• CAS No.: 1822-66-8
• Molecular Formula: C10H12O6S
• Molecular Weight: 260.268
• Hs Code.: 2934999090
• European Community (EC) Number: 623-934-6
• NSC Number: 57502
• DSSTox Substance ID: DTXSID80288763
• Nikkaji Number: J651.768D
• Mol file: 1822-66-8.mol

Synonyms:1822-66-8;Diethyl 3,4-dihydroxythiophene-2,5-dicarboxylate;3,4-Dihydroxythiophene-2,5-dicarboxylic acid diethyl ester;Diethyl 3,4-dihydroxy-thiophene-2,5-dicarboxylate;3,4-dihydroxy-thiophene-2,5-dicarboxylic acid diethyl ester;NSC57502;2,5-Thiophenedicarboxylic acid, 3,4-dihydroxy-, diethyl ester;2,5-dicarbethoxy-3,4-dihydroxythiophene;Diethyl3,4-dihydroxythiophene-2,5-dicarboxylate;2,5-diethyl 3,4-dihydroxythiophene-2,5-dicarboxylate;SCHEMBL1141274;DTXSID80288763;YOKOBAHUBJPMGP-UHFFFAOYSA-N;AMY12160;dicarbethoxy-3.4-dihydroxythiophene;MFCD03094035;NSC-57502;AKOS015898857;AB13298;3,4-dihydroxy-2,5-dicarbethoxythiophene;AC-25756;DS-18408;2,5-diethoxycarbonyl-3,4-dihydroxythiophene;CS-0151860;FT-0756223;E76299;A812672;diethyl 3,4-dihydroxythiophene-2.5-dicarboxylate;3,4-dihydroxythiophen-2,5-dicarboxylic acid diethyl ester;3,4-Dihydroxy-2,5-thiophenedicarboxylic acid, diethyl ester;2,5-THIOPHENEDICARBOXYLIC ACID, 3,4-DIHYDROXY-, 2,5-DIETHYL ESTER;2,5-bis[ethoxy(hydroxy)methylene]tetrahydrothiophene-3,4-dione;InChI=1/C10H12O6S/c1-3-15-9(13)7-5(11)6(12)8(17-7)10(14)16-4-2/h11-12H,3-4H2,1-2H

Chemical Property of Diethyl 3,4-dihydroxythiophene-2,5-dicarboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 132-135 °C(lit.)
• Refractive Index: n20/D 1.4589
• Boiling Point: 343.8 °C at 760 mmHg
• PKA: 8.40±0.20(Predicted)
• Flash Point: 161.7 °C
• PSA: 121.30000
• Density: 1.507 g/cm³
• LogP: 1.51270
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 260.03545927
• Heavy Atom Count: 17
• Complexity: 267

Purity/Quality:

99% ^*data from raw suppliers

3,4-Dihydroxythiophene-2,5-dicarboxylicAcidDiethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): TXi
• Hazard Codes: T,Xi
• Statements: 61-20/21-36-36/37/38
• Safety Statements: 53-45-36-26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C(=C(S1)C(=O)OCC)O)O
• Uses: 3,4-Dihydroxythiophene-2,5-dicarboxylic Acid Diethyl Ester is an intermediate used to prepare alkylenedioxythiophene monomers to obtain electrochromic conducting polymers.

Technology Process of Diethyl 3,4-dihydroxythiophene-2,5-dicarboxylate

There total 3 articles about Diethyl 3,4-dihydroxythiophene-2,5-dicarboxylate 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: 77.0%

diethyl thioglycolate (925-47-3) + oxalic acid diethyl ester (95-92-1) → 3,4-dihydroxythiophene-2,5-dicarboxylic acid diethyl ester (1822-66-8)

Guidance literature:

diethyl thioglycolate; oxalic acid diethyl ester; With ethanol; sodium; at 0 - 25 ℃; for 25h; Inert atmosphere;

With hydrogenchloride; In water; pH=2; Inert atmosphere;

DOI:10.1039/c4ra13060j

Reference yield:

diethyl 3,4-dihydroxythiophene-2,5-dicarboxylate disodium salt (14282-56-5) → 3,4-dihydroxythiophene-2,5-dicarboxylic acid diethyl ester (1822-66-8)

Guidance literature:

With hydrogenchloride; In water;

Reference yield:

→ 3,4-dihydroxythiophene-2,5-dicarboxylic acid diethyl ester (1822-66-8)

Guidance literature:

upstream raw materials:

diethyl thioglycolate

oxalic acid diethyl ester

diethyl 3,4-dihydroxythiophene-2,5-dicarboxylate disodium salt

Downstream raw materials:

3,4-Dibutoxy-thiophene-2,5-dicarboxylic acid diethyl ester

3,4-Bis-decyloxy-thiophene-2,5-dicarboxylic acid diethyl ester

diethyl 3,4-bis(benzyloxy)thiophene-2,5-dicarboxylate

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

Refernces

• 1、 Soganci, Tugba,Kurtay, Gülbin,Ak, Metin,Güllü, Mustafa. "Preparation of an EDOT-based polymer: Optoelectronic properties and electrochromic device application". . p. 2630 - 2639. Retrieved 2015/02/05.
• 2、 -. "Preparation method of 3,4-ethylenedioxythiophene". Paragraph 0074-0082. . Retrieved 2013/03/26.