19432-68-9

Usage

Uses

Methyl 2-Thiopheneacetate can be used as a substrate for penicillin amidase on Eupergit C.

InChI:InChI=1/C7H8O2S/c1-9-7(8)5-6-3-2-4-10-6/h2-4H,5H2,1H3

Upstream product

• 186581-53-3 diazomethane 
• 5271-67-0 2-Thiophenecarbonyl chloride 
• 4298-52-6 2-ethynyl-thiophene 
• 67-56-1 methanol 
• 88-15-3 2-Acetylthiophene 
• 20893-30-5 2-cyanomethylthiophene 
• 1918-77-0 Thiophene-2-acetic acid 
• 542-78-9 Malondialdehyde 
• 2365-48-2 Methyl thioglycolate 
• 188290-36-0 thiophene 
• 96-35-5 glycolic acid methyl ester 
• 27757-85-3 2-Aminomethylthiophene 
• 201230-82-2 carbon monoxide 
• 39098-97-0 2-thienylacetic acid chloride 

Downstream Products

• 1918-77-0 Thiophene-2-acetic acid 
• 4461-29-4 2-(thiophen-2-yl)acetamide 
• 105550-86-5 5-(2-cloro-4-nitrobenzoil)tiofen-2-acetato di metile 
• 5402-55-1 2-thiophenethanol 
• 934176-81-5 (5-{2-[2-(2',3',4'-trimethoxy-biphenyl-3-yl)-acetylamino]-phenyl}-thiophen-2-yl)-acetic acid methyl ester 
• 1219943-64-2 1-(2,4-dimethoxybenzyl)-4-hydroxy-3-(2-thienyl)-1H-pyrrol-2(5H)-one 
• 15022-15-8 2-thienylacetaldehyde 
• 1093351-59-7 C₁₆H₁₀⁽²⁾H₆ClNO₂S 
• 1422495-71-3 (S)-methyl 2-(2-chlorophenyl)-2-(1,1,2,2-tetradeutero-2-(thiophen-2-yl)ethylamino)acetate 
• 153-61-7 cephalothin 
• 5935-65-9 Desacetylcephalothin 
• 35607-66-0 cefoxitin 
• 527-72-0 2-thiophenylcarboxylic acid 

Relevant academic research and scientific papers

One-dimensional optoelectronic nanostructures derived from the aqueous self-assembly of π-conjugated oligopeptides

The aqueous self-assembly of oligopeptide-flanked π-conjugated molecules into discrete one-dimensional nanostructures is described. Unique to these molecules is the fact that the π-conjugated unit has been directly embedded within the peptide backbone by way of a synthetic amino acid with π-functionality that is compatible with standard Fmoc-based peptide synthesis. The peptide-based molecular design enforces intimate π-π communication within the aggregate after charge-screening and self-assembly, making these nanostructures attractive for optical or electronic applications in biological environments. The synthesis and assembly are reported along with spectroscopic and morphological characterization of the new nanomaterials. Copyright

N-acylhydrazones containing thiophene nucleus: a new anticancer class

In this study, we present a series of N-acylhydrazones containing thiophene nuclei as a new anticancer class. Fifty-seven compounds in this series were evaluated for their activity against four human cancer cell lines. Cytotoxicity (IC50) ranged from 0.82 to 12.90 μM. The compound (E)-N′-(2-hydroxy-3-methoxybenzylidene)thiophene-2-carbohydrazide displayed good cytotoxic activity in all cell lines (IC50 = 0.82–5.36 μM) and yielded the best result in this series; therefore, it is an important lead compound in this new class.

Structure–Property Relationships in Bithiophenes with Hydrogen-Bonded Substituents

The use of crystal engineering to control the supramolecular arrangement of π-conjugated molecules in the solid-state is of considerable interest for the development of novel organic electronic materials. In this study, we investigated the effect of combining of two types of supramolecular interaction with different geometric requirements, amide hydrogen bonding and π-interactions, on the π-overlap between calamitic π-conjugated cores. To this end, we prepared two series of bithiophene diesters and diamides with methylene, ethylene, or propylene spacers between the bithiophene core and the functional groups in their terminal substituents. The hydrogen-bonded bithiophene diamides showed significantly denser packing of the bithiophene cores than the diesters and other known α,ω-disubstituted bithiophenes. The bithiophene packing density reach a maximum in the bithiophene diamide with an ethylene spacer, which had the smallest longitudinal bithiophene displacement and infinite 1D arrays of electronically conjugated, parallel, and almost linear N?H???O=C hydrogen bonds. The synergistic hydrogen bonding and π-interactions were attributed to the favorable conformation mechanics of the ethylene spacer and resulted in H-type spectroscopic aggregates in solid-state absorption spectroscopy. These results demonstrate that the optoelectronic properties of π-conjugated materials in the solid-state may be tailored systematically by side-chain engineering, and hence that this approach has significant potential for the design of organic and polymer semiconductors.

B(C6F5)3-catalyzed O-H insertion reactions of diazoalkanes with phosphinic acids

A highly efficient base-, metal-, and oxidant-free catalytic O-H insertion reaction of diazoalkanes and phosphinic acids in the presence of B(C6F5)3has been developed. This powerful methodology provides a green approach towards the synthesis of a broad spectrum of α-phosphoryloxy carbonyl compounds with good to excellent yields (up to 99% yield). The protocol features the advantages of operational simplicity, high atom economy, practicality, easy scalability and environmental friendliness.

Thiophene-based water-soluble fullerene derivatives as highly potent antiherpetic pharmaceuticals

Here we report the Friedel-Crafts arylation of chlorofullerenes C60Cl6 and C70Cl8 with thiophene-based methyl esters. While C60Cl6 formed expected Cs-C60R5Cl products, C70Cl8 demonstrated a tendency for both substitution of chlorine atoms and addition of an extra thiophene unit, thus forming Cs-C70R8 and C1-C70R9H compounds. The synthesized water-soluble C60 and C70 fullerene derivatives with thiophene-based addends demonstrated high activity against a broad range of viruses, including human immunodeficiency virus, influenza virus, cytomegalovirus, and herpes simplex virus. The record activity of C70 fullerene derivatives against herpes simplex virus together with low toxicity in mice makes them promising candidates for the development of novel non-nucleoside antiherpetic drugs.

Exploiting excited-state aromaticity to design highly stable singlet fission materials

Singlet fission, the process of forming two triplet excitons from one singlet exciton, is a characteristic reserved for only a handful of organic molecules due to the atypical energetic requirement for low energy excited triplet states. The predominant strategy for achieving such a trait is by increasing ground state diradical character; however, this greatly reduces ambient stability. Herein, we exploit Baird's rule of excited state aromaticity to manipulate the singlet-triplet energy gap and create novel singlet fission candidates. We achieve this through the inclusion of a [4n] 5-membered heterocycle, whose electronic resonance promotes aromaticity in the triplet state, stabilizing its energy relative to the singlet excited state. Using this theory, we design a family of derivatives of indolonaphthyridine thiophene (INDT) with highly tunable excited state energies. Not only do we access novel singlet fission materials, they also exhibit excellent ambient stability, imparted due to the delocalized nature of the triplet excited state. Spin-coated films retained up to 85% activity after several weeks of exposure to oxygen and light, while analogous films of TIPS-pentacene showed full degradation after 4 days, showcasing the excellent stability of this class of singlet fission scaffold. Extension of our theoretical analysis to almost ten thousand candidates reveals an unprecedented degree of tunability and several thousand potential fission-capable candidates, while clearly demonstrating the relationship between triplet aromaticity and singlet-triplet energy gap, confirming this novel strategy for manipulating the exchange energy in organic materials.

Synergistic Catalysis for the Umpolung Trifluoromethylthiolation of Tertiary Ethers

The first transition-metal-free, site-specific umpolung trifluoromethylthiolation of tertiary alkyl ethers has been developed, achieving the challenging tertiary C(sp3)–SCF3 coupling under redox-neutral conditions. The synergism of organophotocatalyst 4CzIPN and BINOL-based phosphorothiols can site-selectively cleave tertiary sp3 C(sp3)–O ether bonds in complex molecules initiated by a polarity-matching hydrogen-atom-transfer (HAT) event. The incorporation of several competing benzylic and methine C(sp3)?H bonds in alkyl ethers has little influence on the regioselectivity. Selective difluoromethylthiolation of C?O bonds has also been achieved. This represents not only an important step forward in trifluoromethylthiolation but also a promising means for site-selective C?O bond functionalization of unsymmetrical tertiary alkyl ethers.

Compounding method for 2-thiopheneacetyl chloride

The invention discloses a compounding method for 2-thiopheneacetyl chloride and belongs to the technical field of organic synthesis. The 2-thiopheneacetyl chloride is compounded by taking thiophene asa raw material through following three-step reaction: 1) acquiring 2-thiophene acetate through the F-C reaction of thiophene and glycolate under the existence of catalyst; 2) hydrolyzing the 2-thiophene acetate under the existence of acid, thereby acquiring 2-thiopheneacetic acid; 3) treating the 2-thiopheneacetic acid in the manner of acylating chlorination with thionyl chloride under the catalysis of pyridine, thereby acquiring 2-thiopheneacetyl chloride. The compounding method for 2-thiopheneacetyl chloride has the characteristics of easily acquired raw materials and simple and convenientoperation and is suitable for industrial production.

Method for preparing 2-thiophenecarboxylic acid

The invention provides a method for preparing 2-thiophenecarboxylic acid. The method comprises that 1, 3-malonaldehyde and a compound A undergo a ring-closure reaction to produce a 2-thiophene ester compound and the 2-thiophene ester compound is hydrolyzed into 2-thiophenecarboxylic acid. The method is simple. Compared with the prior art with a complicated production method and harsh production conditions, the method using a one-pot method can realize the synthesis of the target product. Compared with the existing multi-step synthesis process, the method improves a yield by at least 50%. The method optimizes the production process and the synthesis route. In the production process, side reactions are few, a selective reaction is avoided, impurities are few, post-treatment is convenient, production conditions are mild and method is suitable for an industrialized production mode.

Palladium-Catalyzed Carbonylative Direct Transformation of Benzyl Amines under Additive-Free Conditions

In this communication, we developed a new procedure for the direct carbonylative transformation of benzyl amines. Using dimethyl carbonate as the solvent, methyl 2-arylacetates can be produced in good to excellent yields from the corresponding primary, secondary, and tertiary benzyl amines with palladium as the catalyst. Notably, no base or any other additive is required here. In addition, our procedure can also be applied in the preparation of methylphenidate, which is a marketing drug and used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy.