925-47-3

Usage

Uses

Used in Pharmaceutical Industry:
DIETHYL THIOGLYCOLATE 96 is used as a synthetic intermediate for the production of potent anticonvulsant agents. These agents are crucial in the development of medications that help control seizures and other neurological disorders.
Used in Polymer and Solar Cell Industry:
DIETHYL THIOGLYCOLATE 96 is used as a precursor in the preparation of thienophenanthrene derivatives. These derivatives are essential components in the manufacturing of polymer light-emitting devices and solar cells, contributing to advancements in energy efficiency and renewable energy technologies.

InChI:InChI=1/C8H14O4S/c1-3-11-7(9)5-13-6-8(10)12-4-2/h3-6H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 123-93-3 thiodiacetic acid 
• 105-39-5 chloroacetic acid ethyl ester 
• 623-73-4 diazoacetic acid ethyl ester 
• 13001-80-4 bis-(2-chloro-2-ethoxy-vinyl)-sulfane 
• 623-51-8 ethyl 2-sulfanylacetate 
• 4455-13-4 methylthioacetic acid ethyl ester 
• 105-36-2 ethyl bromoacetate 
• 5187-82-6 (ethoxycarbonylmethyl)dimethylsulfonium bromide 

Downstream Products

• 4282-31-9 Thiophene-2,5-dicarboxylic acid 
• 62497-27-2 3,4-bis(4-methylphenyl)thiophene-2,5-dicarboxylic acid 
• 5447-21-2 bis(hydrazinocarbonylmethyl)sulphide 
• 68116-55-2 4,4'-dimethyl-α,α'-sulfanediyl-di-cinnamic acid 
• 68116-53-0 α,α'-sulfanediyl-di-cinnamic acid 
• 19799-43-0 3,4-bis-(4-chloro-phenyl)-thiophene-2,5-dicarboxylic acid 
• 1822-66-8 3,4-dihydroxythiophene-2,5-dicarboxylic acid diethyl ester 
• 19799-42-9 3,4-bis(phenyl)thiophene-2,5-dicarboxylic acid 
• 854627-48-8 3-methyl-4-phenyl-thiophene-2,5-dicarboxylic acid 
• 14618-65-6 thiodiglcollic acid bis-amide 
• 14282-56-5 diethyl 3,4-dihydroxythiophene-2,5-dicarboxylate disodium salt 
• 18361-03-0 3,4-ethylenedioxythiophene-2,5-dicarboxyllic acid 
• 1332863-62-3 N-nitroso-2,6-dicarbethoxy-3,5-diphenyltetrahydro-1,4-thiazine-1,1-dioxide 

Relevant academic research and scientific papers

Synthesis of 2,6-dicarbethoxy-3,5-diaryltetrahydro-1,4-thiazine-1,1-dioxide derivatives as potent anticonvulsant agents

Abstract An efficient synthesis of 2,6-dicarbethoxy-3,5-diaryltetrahydro-1,4-thiazine-1,1-dioxide derivatives has been achieved under aqueous medium for the first time in good to excellent yields. All the synthesized compounds were tested for anticonvulsant activity using the maximal electroshock (MES), subcutaneous pentylenetetrazole (scPTZ) screens, which are the most broadly employed seizure models for early identification of candidate anticonvulsants. Their neurotoxicity was determined applying the rotarod test. Seven compounds 4a, 4d, 4f, 4h, 4o, 4p and 4q showed promising anticonvulsant activities in both models employed for anticonvulsant evaluation. The most active compound 4d showed the MES-induced seizures with ED50 value of 10.2 mg/kg and TD50 value of 288.6 mg/kg after intraperitoneal injection to mice, which provided compound 4d with a protective index (TD50/ED50) of 28.3 in the MES test.

Polymer material monomer 3, 4 - ethylene dioxy thiophene preparation method

The invention relates to a method for preparing polymer monomer 3,4-ethylenedioxythiophene. The method includes firstly dissolving ethyl chloroacetate and sodium sulphide in acetone to react to obtain diethyl thioglycolate; secondly, dissolving the diethyl thioglycolate to ethanol, adding sodium ethoxide and diethyl oxalate into the ethanol, heating and reflowing to obtain ethanol solution of 2,5-dioctyl phthalate ethyl ester-3,4-thiophene glycol sodium; thirdly, adding dichloroethane and tetrabutylammonium bromide into the ethanol solution of the 2,5-dioctyl phthalate ethyl ester-3,4-thiophene glycol sodium, heating and reflowing to obtain 3,4-ethylenedioxy-2,5-dioctyl phthalate ethyl ester thiophene; fourthly, dissolving the 3,4-ethylenedioxy-2,5-dioctyl phthalate ethyl ester thiophene in mixed solvent, adding sodium chloride, heating and reacting, and finally reducing pressure and rectifying. The method for preparing polymer monomer 3,4-ethylenedioxythiophene is few in procedures, low in cost, safe and reliable in technique, simple and fast in post-treatment method, and products are high in yield and purity.

Aminothiophene sulfonic acid ester

PROBLEM TO BE SOLVED: To provide 3,4-disubstituted thiophene sulfonate usable as a monomer for a conductive polymer, and not having carboxylate on 2,5-positions, and to provide a method for producing the same.SOLUTION: This thiophene sulfonate is represented by general formula (1). The thiophene sulfonate is obtained, for example, by decarboxylation of 3,4-dihydroxy-2,5-dicarboxylic acid thiophene in a basic inert solvent, followed by reaction with sulfonyl chlorides in the presence of a tertiary alkylamine catalyst. (In the formula, Rand Reach independently represent a 1-8C alkyl, phenyl or tolyl).

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 of an EDOT-based polymer: Optoelectronic properties and electrochromic device application

Here we present the synthesis, characterization and electropolymerization of a new EDOT-based monomer; 5,10-dihydrobenzo[f]thieno[3,4-b][1,4]dioxocine (DTD). Electrochemical polymerization of DTD was performed potentiostatically by using dichloromethane (DCM) as solvent and tetrabutylammonium hexafluorophosphate (TBPF6) as supporting electrolyte. Homopolymer [P(DTD)] films and copolymer [P(DTD-co-TPA)] films of DTD prepared by using 4-(2,5-di(thiophen-2-yl)-1H-pyrrole-1-yl)butane-1-amine (TPA) were characterized via CV and UV-vis spectroscopy. Spectroelectrochemical analysis of P(DTD) revealed electronic transitions at 585 nm (π-π transition) with an electronic band gap of 1.69 eV. Electrochromic studies revealed that P(DTD) has competitive properties to EDOT. Furthermore, a dual-type complementary colored polymer electrochromic device based on P(DTD) and P(TPA) was constructed in sandwich configuration. Spectroelectrochemical studies revealed that the oxidized state of the device shows a blue color whereas it is yellow in the reduced state. The maximum contrast (Δ%T) and switching time of the device were measured as 25.5% and 0.5 s for 385 nm and 21% and 1.0 s for 550 nm.

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.

L-proline-catalyzed three-component domino [3+2+1] annulation for the regio- and diastereoselective synthesis of highly substituted thienothiopyrans containing three or four stereocenters

(Chemical Equation Presented) L-Proline-catalyzed three-component reactions of ethyl 2-[(2-oxo-2-arylethyl)sulfonyl]acetate or ethyl 2-[(2-ethoxy-2- oxoethyl)sulfonyl]acetate, aromatic aldehydes, and 5-aryltetrahydro-3- thiophenone furnished a variety of highly substituted thieno[3,2-c]thiopyran derivatives. This facile transformation presumably occurs via a one-pot domino sequence of enamine formation/aldol condensation/Michael addition/6-exo-trig cyclization/elimination and involves the creation in a single operation of three C-C bonds and the generation of three new stereocenters with complete diastereoselectivity in all cases and a fourth one in ca. 7:3 diastereomeric ratio when starting from a 5-substituted tetrahydro-3-thiophenone derivative.

PROCESS FOR PREPARING DIALKYL THIODIGLYCOLATES

A process is described for preparing alkyl thiodiglycolates of the general formula (I) [in-line-formulae]R—OOC—CH2-S—CH2-COO—R ??(I)[/in-line-formulae] where R is a radical of branched or unbranched C1 to C10-alkyl, characterized in that an alkyl haloacetate of the general formula (II) [in-line-formulae]X—CH2-COO—R ??(II)[/in-line-formulae] where X is a chlorine or bromine atom and R is as defined for compounds of the formula (I) is reacted with an aqueous solution of alkali metal sulphide or alkali metal hydrogensulphide in the presence of an aqueous pH buffer solution in the pH range between 5 and 8, optionally in the presence of a phase transfer catalyst.

Synthesis and anticonvulsant activity of some new bishydrazones derived from 3,4-dipropyloxythiophene

A series of new 3,4-dipropyloxy-N2,N5-bis(substituted)thiophene-2,5-dicarbohydrazides (4-30) were synthesized from ethyl thiodiglycolate and diethyloxalate through multistep reactions. Following Dieckmann-Komppa reaction, the required precursor 3,4-dihydroxythiophene-2,5-diester (1) was prepared. This was derivatized with propyl bromide and further converted to corresponding hydrazide (3), which was finally transformed to targeted hydrazones (4-30) by conventional methods. The newly synthesized compounds were characterized using FT-IR, 1H and 13C NMR, EI-MS and elemental analyses. The anticonvulsant activity of all the title compounds was investigated against maximal electroshock induced seizures (MES) and subcutaneous pentylenetetrazole (scMET) models and their neurotoxicity was also evaluated. Some of the selected compounds were subjected to 6 Hz test in order to evaluate their uncover activities. Compound 3,4-dipropyloxy-N2,N5-bis[1-(2-thienyl)ethylidene]thiophene-2,5-dicarbohydrazide (15) has emerged as a lead in this series with less neurotoxicity.