1451-95-2

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
Thiophene-2,3-dicarboxylic acid is utilized as a key intermediate in the development of various pharmaceuticals and agrochemicals. Its unique structure allows for the creation of novel compounds with potential therapeutic and pesticidal properties, contributing to advancements in healthcare and agriculture.
Used in Organic Electronics and Semiconductors:
As a component in thiophene-based polymers, Thiophene-2,3-dicarboxylic acid plays a crucial role in the fabrication of organic electronic devices and semiconductors. Its incorporation enhances the performance and stability of these devices, paving the way for innovations in flexible electronics and energy-efficient technologies.
Used in Optoelectronic Devices:
Thiophene-2,3-dicarboxylicacid's properties make it suitable for use in optoelectronic devices, where it can improve light absorption, charge transport, and overall device efficiency. This contributes to the development of high-performance solar cells, light-emitting diodes (LEDs), and other optoelectronic applications.
Used in Dye and Pigment Production:
Thiophene-2,3-dicarboxylic acid is employed in the manufacture of dyes and pigments, offering a range of color options and properties for various industries, including textiles, plastics, and printing inks.
Used as a Reagent in Organic Synthesis:
In the realm of organic chemistry, Thiophene-2,3-dicarboxylic acid serves as a valuable reagent, facilitating a variety of chemical reactions and syntheses. Its versatility in this context supports the development of new chemical compounds and materials.
Used in Specialty Chemicals and Materials Production:
Due to its distinctive structural and chemical attributes, Thiophene-2,3-dicarboxylic acid has potential industrial applications in the production of specialty chemicals and materials, where it can impart specific properties or functions to the final products.

InChI:InChI=1/C4H2N2OS/c7-3-6-4-5-1-2-8-4/h1-2H

Upstream product

• 13679-72-6 2-acetyl-3-methylthiophene 
• 1918-78-1 2-methylthiophene-3-carboxylic acid 
• 527-72-0 2-thiophenylcarboxylic acid 
• 124-38-9 carbon dioxide 
• 18853-42-4 2,3-Dicyanothiophene 
• 7311-64-0 3-bromothiophene-2-carboxylic acid 
• 97759-73-4 2-(3-carboxy-2-thienyl)-4,4-dimethyloxazoline 
• 98331-03-4 2-(N-tert-butylcarbamoyl)thiophene-3-carboxylic acid 
• 88-13-1 3-Thiophene carboxylic acid 
• 23806-24-8 3-methyl-2-thiophenecarboxylic acid 
• 632-16-6 2,3-dimethylthiophene 
• 5271-67-0 2-Thiophenecarbonyl chloride 
• 90642-98-1 N-(tert-butyl)thiophene-2-carboxamide 
• 765-50-4 2-Chloromethylthiophene 

Downstream Products

• 14300-68-6 2,3-Thiophendicarbonsaeure-dimethylester 
• 115777-72-5 2-methoxycarbonyl-3-thiophenecarboxylic acid 
• 6007-83-6 2,3-thiophenedicarboxylic acid anhydride 
• 250-65-7 thieno[3,4-b]thiophene 

Relevant academic research and scientific papers

Synthesis and cytotoxicity of Methyl-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione derivatives

2- and 3-Methyl-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione and related derivatives were synthesized and evaluated in vitro by NCI against eight cancer types. Compounds 12-15 showed significant activity against melanoma, NCI-H23 non-small cell lung cancer, and MDA-MB-435 and MDA-N breast cancer cell lines; 2-hydroxymethyl-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione (13) showed the highest activity against melanoma (mean log GI50=-7.74) and the highest overall potency (mean log GI50=-6.99). Copyright (C) 1999 Published by Elsevier Science Ltd.

Solvent evaporation method and crystal structure of thiophene-2,3-dicarboxylate

One new thiophene compound i.e. , thiophene-2,3-dicarboxylate with 2,3-dibromo thiophene, butyllithium and anhydrous ether has been successfully synthesized. The compound has been characterized by X-ray single-crystal diffraction. The new synthesized compound shows a one-dimensional framework. The 3D supramolecular structure is formed via hydrogen bonding connection.

Facile access to novel 1,4-dihydroxynaphthalene-2,3-dicarboximides and heterofused analogs

A variety of novel 1,4-dihydroxynaphthalene-2,3-dicarboximides and heterofused analogs were prepared by a convenient one-pot base-catalyzed condensation of N-substituted succinimides with aromatic ortho diester derivatives.

Thiophene bioisosteres of GluN2B selective NMDA receptor antagonists: Synthesis and pharmacological evaluation of [7]annuleno[b]thiophen-6-amines

Thiophene bioisosteres of potent GluN2B receptor negative allosteric modulators were prepared and evaluated pharmacologically. The five-step synthesis of 4,5,7,8-tetrahydro[7]annuleno[b]thiophen-6-one (10) was considerably improved by carboxylation of thiophene-3-carboxylic acid (8) in the first reaction step. Reductive amination and alkylation led to three homologous series of secondary and tertiary phenylalkylamines 5, 11 and 12. Metalation, reaction with 1-formylpiperidine and subsequent reduction provided hydroxymethyl derivatives 15 and 16, which had been designed as bioisosteres of phenols. 2-Bromo derivatives 18 were obtained by bromination of ketone 10 with NBS and subsequent reductive amination. High GluN2B affinity was achieved with [7]annuleno[b]thiophenes bearing a 3-phenylpropylamino or 4-phenylbutylamino moiety (e.g. 5c: Ki = 5.9 nM; 11d: Ki = 9.0 nM). Tertiary ethylamines 12 showed lower GluN2B affinity than tertiary methylamines 11 or secondary amines 5 (e.g. 5c: Ki = 5.9 nM; 11c: Ki = 6.0; 12c: Ki = 51 nM). A Br-atom or a hydroxymethyl moiety in 2-position were less tolerated by the GluN2B receptor. Very similar relationships between the structure and GluN2B affinity and structure and σ affinity, in particular σ2 affinity, were detected. A slight preference for the ifenprodil binding site of GluN2B receptors over σ1 and σ2 receptors was found for methylamines 11c (≈2-fold) and 11d (≈1.5–2-fold) as well as for bromo derivative 18c (≈3-fold).

BENZOBIS-(THIADIAZOLE) DERIVATIVE, INK CONTAINING THE SAME, AND ORGANIC ELECTRONICS DEVICE USING THE SAME

The object of the present invention is to provide a benzobis-(thiadiazole) derivative which has excellent electron mobility (field-effect mobility) and excellent stability in the atmosphere. The present invention relates to a benzobis-(thiadiazole) derivative which has a cyclic imide structure with condensed aromatic ring in its molecule shown in the formula (1) or (2): (In the formula, R, A and Z represent specific groups.)

Dynamic combinatorial chemistry with novel dithiol building blocks: Towards new structurally diverse and adaptive screening collections

We describe the synthesis of a range of novel dithiol-functionalized building blocks and demonstrate how they can be used to generate new structurally diverse dynamic combinatorial libraries. A proof-of-principle experiment using the catecholamine dopamine revealed that molecular recognition changed the library composition under biocompatible conditions and identified new promising candidate receptors of this biologically important neurotransmitter. Georg Thieme Verlag Stuttgart - New York.

ORGANIC SEMICONDUCTOR MATERIAL

The present invention relates to a novel compounds useful as organic semiconductor material, and semiconductor devices containing said organic semiconductor material.

Synthesis of thieno[3,4-b]thiophene, thieno[3,4-b]furan, related compounds and their derivatives and use thereof

Inexpensive and facile methods of preparing fused heterocycles such as thieno[3,4-b]thiophene, thieno[3,4-b]furan, related compounds, and their derivatives are disclosed. Also disclosed are regioregular polymers prepared from the fused heterocycles.

Synthesis of mono- and bisadducts of thieno-o-quinodimethane with c 60 for efficient polymer solar cells

A series of mono- and bisadducts of thieno-o-quinodimethane with C 60 (TOQC) was efficiently prepared through the Diels-Alder reaction of pristine or solubilizing side-chain-substituted 2,3-bis(chloromethyl) thiophene with C60. The pristine TOQC bisadduct (bis-TOQC) shows much higher performance than the side-chain-substituted TOQC bisadducts in polymer solar cells, while the situation is inverse for the TOQC monoadducts. The best power conversion efficiency of 5.1% was achieved from the bis-TOQC:P3HT solar cells under simulated AM1.5G irradiation (86 mW/cm2).

Thienopyrrolyl dione end-capped oligothiophene ambipolar semiconductors for thin film- and light emitting transistors

The design, synthesis and structure-property investigation of a new thienopyrrolyl dione substituted oligothiophene material showing reduced band gap energy, low lying LUMO energy level and ambipolar semiconducting behaviour is described.