18361-03-0

Basic information

• Product Name: 2,5-Dicarboxylic acid-3,4-ethylene dioxythiophene
• Synonyms: 2,3-Dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid;2, 5 - dicarboxylic acid - 3, 4 - thiophene ethylene 2 oxygen;3,4-Ethylenedioxythiophene-2,5-dicarboxylic Acid;3,4-ETHYLENEDIOXOTHIOPHENE-2,5-DICARBOXYLIC ACID;2,3-Dihydro-thieno[3,4-b]-p-dioxin-5,7-dicarboxylic acid;Thieno[3,4-B]-1,4-Dioxin-5,7-DicarboxylicAcid,2,3-Dihydro-;3,4-Ethylendioxythiophen-2,5-dicarbonsure;2,5-Dicarboxylic acid-3,4-ethylene dioxythiophene
• CAS NO: 18361-03-0
• Molecular Formula: C₈H₆O₆S
• Molecular Weight: 230.19464
• EINECS: 201-215-5
• Product Categories: API intermediates;Thiophenes
• Mol File: 18361-03-0.mol

Chemical Properties

• Melting Point: 319.5-321.2 °C
• Boiling Point: 482.6 °C at 760 mmHg
• Flash Point: 245.6 °C
• Appearance: /
• Density: 1.732 g/cm³
• Vapor Pressure: 4.01E-10mmHg at 25°C
• Refractive Index: 1.663
• Solubility: slightly sol. in Dimethylformamide
• PKA: 3.56±0.20(Predicted)
• CAS DataBase Reference: 2,5-Dicarboxylic acid-3,4-ethylene dioxythiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dicarboxylic acid-3,4-ethylene dioxythiophene(18361-03-0)
• EPA Substance Registry System: 2,5-Dicarboxylic acid-3,4-ethylene dioxythiophene(18361-03-0)

Safety Data

• Hazardous Substances Data: 18361-03-0(Hazardous Substances Data)

Usage

Uses

2,3-Dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid is a useful reactant for a metal-?organic framework biosensor that was used to detect ascorbic acid (AA).

InChI:InChI=1/C8H6O6S/c9-7(10)5-3-4(14-2-1-13-3)6(15-5)8(11)12/h1-2H2,(H,9,10)(H,11,12)

Upstream product

• 553-90-2 Dimethyl oxalate 
• 925-47-3 diethyl thioglycolate 
• 14282-56-5 diethyl 3,4-dihydroxythiophene-2,5-dicarboxylate disodium salt 
• 107-06-2 1,2-dichloro-ethane 
• 95-92-1 oxalic acid diethyl ester 
• 75-34-3 1,1-dichloroethane 
• 58416-04-9 3,4-dihydroxythiophene-2,5-dicarboxylic acid dimethyl ester 
• 67-63-0 isopropyl alcohol 
• 1822-66-8 3,4-dihydroxythiophene-2,5-dicarboxylic acid diethyl ester 
• 154934-13-1 2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid diethyl ester 

Downstream Products

• 1263307-13-6 N,N'-bis(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylthiocarbamoyl)-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxamide 
• 1263307-11-4 N,N'-bis(benzylthiocarbamoyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxamide 
• 1263307-10-3 N,N'-bis(2,6-dimethylphenylthiocarbamoyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxamide 
• 1263307-09-0 C₂₂H₁₈N₄O₄S₃ 
• 1263307-08-9 C₃₀H₂₈N₆O₆S 
• 1263307-06-7 C₂₂H₂₀N₂O₄S 
• 1263307-05-6 N,N'-bis(2,6-dimethylphenyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxamide 
• 1269935-37-6 2,5-bis(N-phenylamidino)-3,4-ethylenedioxythiophene 
• 1269767-32-9 C₂₀H₁₄Cl₂N₂O₂S 
• 1263307-04-5 N,N'-diphenyl-2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxamide 
• 174508-31-7 5,7-dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine 
• 126213-50-1 3,4-(ethylenedioxy)thiophene 

Relevant articles and documents

Preparation method of 3,4-ethylene dioxy thiophene

The invention relates to a preparation method of organic matter, in particular to a preparation method of 3,4-ethylene dioxy thiophene.With chloracetate as the initial raw material, 3,4-ethylene dioxy thiophene is preparated through vulcanization reaction, condensation, etherification, saponification and decarboxylic reaction.The method is easy to operate, low in cost, safe, environmentally friendly, high and stable in product yield, good in product color and luster, simple in process during reaction, not strict in reaction condition and quite suitable for industrial production.

Preparation method of 3,4-ethylenedioxythiophene

A method of preparing 3,4-ethylenedioxythiophene is provided. The preparation is performed by microwave heating to greatly increase the yield and decrease the reaction time, energy consumption, solvent usage, and environmental damage.

An improved procedure for the synthesis of 3,4-ethylenedioxythiophene

An improved procedure for the synthesis of 3,4-ethylenedioxythiophene is reported starting from ethyl chloroacetate. Reaction with sodium sulfide gave diethyl thiodiglycolate which was then reacted with diethyl oxalate, and then 1,2-dibromoethane to give 2,5-dicarbethoxy-3,4-ethylenedioxythiophene. Hydrolysis, and decarboxylation gave 3,4-ethylenedioxythiophene in 16% overall yield. The structures of the key intermediates in synthetic routes were confirmed, and every step was optimised, to give a procedure suitable for large-scale industrial production.

The first direct experimental comparison between the hugely contrasting properties of PEDOT and the all-sulfur analogue PEDTT by analogy with well-defined EDTT-EDOT copolymers

The structures of poly(3,4-ethylenedioxythiophene) (PEDOT) and poly(3,4-ethylenedithiathiophene) (PEDTT) vary only in the substituent chalcogen atoms, yet the electronic properties of the materials are surprisingly dissimilar. The difference in electronic band gaps is approximately 0.8 eV and the polymers behave very differently upon p-doping. Two new terthiophenes have been synthesised using Negishi coupling methods. The X-ray crystal structures of EDOT-EDTT-EDOT (OSO) and EDTT-EDOT-EDTT (SOS) show strong intramolecular chalcogen-chalcogen contacts which are responsible for persistent conformers in solution and solid state, although significant interchain interactions should also influence the properties of the materials. SOS and OSO can be polymerised by electrochemical oxidation to give the corresponding, well-defined poly(terthiophenes) PSOS and POSO. Spectroelectrochemical studies on all four polymers reveal strong similarities between PEDTT and PSOS, and between PEDOT and POSO. Together with independent electrochemical and absorption studies, the results indicate that the unique properties of PEDOT are influenced more by conformational effects (intrachain S...O contacts) than substituent effects. The Royal Society of Chemistry 2005.

Process for the alkylation of 3,4-dihydroxythiophene-2,5-dicarboxylic esters

The invention relates to a process for the alkylation of 3,4-dihydroxythiophene-2, 5-dicarboxylic esters or their alkali metal or alkaline earth metal salts with alkylating agents in a polar diluent in the presence of quaternary onium salts.

Process for the preparation of 3,4-alkylenedioxythiophene-2,5-dicarboxylic acid derivatives

A process for the preparation of 3,4-alkylenedioxythiophene-2,5- dicarboxylic acid derivatives selected from the group consisting of compounds of the general formulae IV and V:comprising carrying out at least 2 steps in accordance with formula scheme 1 without isolation of intermediates, wherein R1, R2, R3 and R4 are identical or different and are a linear or branched, optionally substituted alkyl radical having 1 to 20 carbon atoms, A is lithium, sodium or potassium, and Hal is fluorine, chlorine, bromine or iodine, wherein the formula scheme 1 comprises:

Process for the preparation of 3, 4-alkylenedioxythiophene-2,5-dicarboxylic acid derivatives

A process for the preparation of 3,4-alkylenedioxythiophene-2,5-dicarboxylic acid derivatives of the general formulae IV and V characterized in that at least 2 steps in accordance with formula scheme 1, in which R1, R2, R3 and R4 are identical or different and are a linear or branched, optionally substituted alkyl radical having 1 to 20 carbon atoms, A is lithium, sodium or potassium, and Hal is fluorine, chlorine, bromine or iodine, are carried out without isolation of the intermediates, gives the target products in high purity and yield.

A facile synthesis of 3,4-dialkoxythiophenes

Dialkylation of diethyl 3,4-dihydroxythiophenedicarboxylate followed by ester hydrolysis and acid decarboxylation provides a general route to 3,4-dialkoxythiophenes.