4282-35-3

Usage

Uses

Used in Pharmaceutical Research:
3,4-Thiophenedicarboxylic acid, dimethyl ester is utilized as an intermediate in the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be a key component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Production:
In the agrochemical industry, 3,4-Thiophenedicarboxylic acid, dimethyl ester serves as an intermediate for the production of various agrochemicals. Its application in this field aids in the development of effective pesticides and other agricultural chemicals that are essential for crop protection and yield enhancement.
Organic Synthesis:
3,4-Thiophenedicarboxylic acid, dimethyl ester is also employed in organic synthesis for the creation of a range of organic compounds. Its versatility in chemical reactions makes it a valuable precursor in the synthesis of specialty chemicals and materials with diverse applications.

Upstream product

• 186581-53-3 diazomethane 
• 4282-29-5 thiophene-3,4-dicarboxylic acid 
• 67-56-1 methanol 
• 5472-38-8 diethyl 2-formylbutanedioate 
• 766-39-2 2,3-Dimethylmaleic anhydride 
• 13314-92-6 dimethyl (Z)-2,3-dimethyl-2-butenedioate 
• 80356-26-9 (E/Z)-Dimethyl 2,3-bis-butenedioate 
• 20946-32-1 3,4-dimethyl 2,5-dihydrothiophene-3,4-dicarboxylate 
• 74-88-4 methyl iodide 
• 73926-95-1 diethyl 2-formyl-3-(diethoxymethyl)succinate 
• 70145-29-8 diethyl 2-(diethoxymethyl)succinate 

Downstream Products

• 18354-73-9 [4-(hydroxymethyl)-3-thienyl]methanol 
• 1393686-92-4 5-(4-nitrophenyl)sulfonyl-4,6-dihydrothieno[3,4-c]pyrrole 
• 99708-92-6 methyl 4-(bromomethyl)thiophene-3-carboxyalte 
• 4282-29-5 thiophene-3,4-dicarboxylic acid 
• 33527-26-3 thiophene-3,4-dicarboxylic acid chloride 

Relevant academic research and scientific papers

Unsymmetrically-Substituted 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-dione Scaffold—A Useful Tool for Bioactive Molecules Design

Unsymmetrically N-substituted and N,N’-disubstituted 5,12-dihydrodibenzo [b,f][1,4]diazocine-6,11-diones were synthesized in the new protocol. The desired modifications of the dibenzodiazocine scaffold were introduced at the stages of proper selection of building blocks as well as post-cyclization modifications with alkylation or acylation agents, expanding the structural diversity and possible applications of synthesized molecules. The extension of developed method resulted in the synthesis of novel: tricyclic 5,10-dihydrobenzo[b]thieno[3,4-f][1,4]diazocine-4,11-dione scaffold and fused pentacyclic framework possessing two benzodiazocine rings within its structure. Additionally, the unprecedented rearrangement of 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-diones to 2-(2-aminophenyl)isoindoline-1,3-diones was observed under the basic conditions in the presence of sodium hydride for secondary dilactams. The structures of nine synthesized products have been established by single-crystal X-ray diffraction analysis. Detailed crystallographic analysis of the investigated tri- and pentacyclic systems has shed more light on their structural features. One cell line derived from non-cancerous cells (EUFA30—human fibroblasts) and three tumor cells (U87—human primary glioblastoma, HeLa—cervix adenocarcinoma, BICR18—laryngeal squamous cell carcinoma) were used to determine the cytotoxic effect of the newly synthesized compounds. Although these compounds showed a relatively weak cytotoxic effect, the framework obtained for 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-dione could serve as a convenient privilege structure for the design and development of novel bioactive molecules suitable for drug design, development and optimization programs.

Single precursor for the synthesis of donor and acceptor units of the low band gap polymers: Synthesis of benzodithiophene and thienopyrroledione from maleic anhydride

An efficient route was developed to synthesize dimethyl thiophene-3,4-dicarboxylate from maleic anhydride. Dimethyl thiophene-3,4-dicarboxylate was used as a single precursor for synthesis of benzo[1,2-b:4,5-b′]dithiophene (BDT) and Thieno[3,4-c]pyrrole-4,6-dione (TPD) derivatives. BDT and TPD derivatives have been highly exploited as donor and acceptor units, respectively, to synthesize important donor-acceptor (D-A) conjugated polymers. BDT-based polymers were found to be one of the most efficient conjugated polymers for organic photovoltaic application. Synthesis of quinone precursor of the dihydroxybenzothiophene was accomplished by a new and unconventional methodology which includes reaction of 3,4-thiophene dicarboxylate with sodium hydride in THF. Dithienobenzoquinone dicarboxylate and dihydroxybenzodithiophene dicarboxylate were characterized structurally by single-crystal X-ray diffraction. Both compounds show strong π-stacking interaction and arrange in the parallel molecular sheets in the crystals.

Synthesis and evaluation of novel heteroaromatic substrates of GABA aminotransferase

Two principal neurotransmitters are involved in the regulation of mammalian neuronal activity, namely, γ-aminobutyric acid (GABA), an inhibitory neurotransmitter, and l-glutamic acid, an excitatory neurotransmitter. Low GABA levels in the brain have been implicated in epilepsy and several other neurological diseases. Because of GABA's poor ability to cross the blood-brain barrier (BBB), a successful strategy to raise brain GABA concentrations is the use of a compound that does cross the BBB and inhibits or inactivates GABA aminotransferase (GABA-AT), the enzyme responsible for GABA catabolism. Vigabatrin, a mechanism-based inactivator of GABA-AT, is currently a successful therapeutic for epilepsy, but has harmful side effects, leaving a need for improved GABA-AT inactivators. Here, we report the synthesis and evaluation of a series of heteroaromatic GABA analogues as substrates of GABA-AT, which will be used as the basis for the design of novel enzyme inactivators.

A facile synthesis of 5,6-dihydro-4H-pyrrolo[3,4-d]thiazole and other pyrrolidine-fused aromatic ring systems via one-step cyclization from diols

A facile synthetic method of 5,6-dihydro-4H-pyrrolo[3,4-d]thiazole, which is a subunit of a potent factor Xa (fXa) inhibitor was developed. This new approach employs one-step cyclization from a diol and can be applied to the syntheses of other pyrrolidine-fused aromatic ring sytems.