5751-80-4

Basic information

• Product Name: Ethyl thiophene-3-carboxylate
• Synonyms: ETHYL 3-THIOPHENEACETATE;ETHYL 3-THIENYLACETATE;ETHYL THIOPHENE-3-CARBOXYLATE;ETHYL THIOPHENE-3-ACETATE;RARECHEM AL BI 0549;ethyl 3-thenoate;Ethylthiophene-3-carboxylate,98%;thiophene-3-carboxylic acid ethyl ester
• CAS NO: 5751-80-4
• Molecular Formula: C₇H₈O₂S
• Molecular Weight: 156.2
• EINECS: 253-665-6
• Mol File: 5751-80-4.mol

Chemical Properties

• Boiling Point: 97-98 °C (8 mmHg)
• Flash Point: 103 °C
• Appearance: /
• Density: 1.12
• Vapor Pressure: 0.18mmHg at 25°C
• Refractive Index: 1.509-1.511
• Storage Temp.: 0-6°C
• Water Solubility: Soluble in water.
• CAS DataBase Reference: Ethyl thiophene-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl thiophene-3-carboxylate(5751-80-4)
• EPA Substance Registry System: Ethyl thiophene-3-carboxylate(5751-80-4)

Safety Data

• Safety Statements: 24/25-23
• Hazardous Substances Data: 5751-80-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Ethyl thiophene-3-carboxylate is used as an intermediate in organic syntheses for the production of various chemicals and pharmaceuticals. Its unique chemical structure allows it to be a versatile building block in the creation of complex molecules, contributing to the development of new compounds with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Ethyl thiophene-3-carboxylate is used as a key intermediate in the synthesis of therapeutic agents. Its ability to form a wide range of derivatives makes it a valuable component in the development of new drugs with specific therapeutic properties.
Used in Chemical Industry:
Ethyl thiophene-3-carboxylate is also utilized in the chemical industry for the production of various specialty chemicals, such as dyes, pigments, and additives. Its unique chemical properties enable it to be a crucial component in the formulation of these products, enhancing their performance and functionality.

InChI:InChI=1/C7H8O2S/c1-2-9-7(8)6-3-4-10-5-6/h3-5H,2H2,1H3

Upstream product

• 41507-35-1 3-thiophene carboxylic acid chloride 
• 64-17-5 ethanol 
• 1468-83-3 1-(thiophen-3-yl)-ethanone 
• 6165-69-1 Thien-3-ylboronic acid 
• 1609-47-8 diethyl dicarbonate 
• 88-13-1 3-Thiophene carboxylic acid 
• 124156-21-4 ethyl (4-methoxyphenylimino)acetate 
• 872-31-1 3-Bromothiophene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 161407-67-6 thiophenfurin 
• 68510-79-2 ethyl 2,5-diphenyl-3-thiophenecarboxylate 
• 1025014-16-7 ethyl 2,5-bis(4-methoxyphenyl)-3-thiophenecarboxylate 
• 1315509-84-2 C₅₄H₈₄O₆S₃Si₃ 
• 1315509-87-5 C₂₇H₂₁Br₃O₆S₃ 
• 1315509-88-6 C₅₇H₆₀O₆S₃ 
• 1315509-83-1 C₂₇H₂₄O₆S₃ 
• 1353717-58-4 C₁₅H₁₃NO₂S 
• 1353717-39-1 ethyl [2-(4-cyanophenyl)thiophen-3-yl]acetate 
• 1353717-61-9 C₁₆H₁₆O₄S 
• 1353717-42-6 methyl 4-(3-ethoxycarbonylmethylthiophen-2-yl)benzoate 
• 1353717-40-4 ethyl [2-(4-nitrophenyl)thiophen-3-yl]acetate 
• 1353717-59-5 C₁₄H₁₃NO₄S 
• 55797-29-0 N-phenyl-3-thiophene-carboxamide 

Relevant articles and documents

4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors

In Gram-negative bacteria, the major mechanism of resistance to β-lactam antibiotics is the production of one or several β-lactamases (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs in an original fashion, and we previously reported its promising potential to yield broad-spectrum inhibitors. However, up to now only moderate antibiotic potentiation could be observed in microbiological assays and further exploration was needed to improve outer membrane penetration. Here, we synthesized and characterized a series of compounds possessing a diversely functionalized alkyl chain at the 4-position of the heterocycle. We found that the presence of a carboxylic group at the extremity of an alkyl chain yielded potent inhibitors of VIM-type enzymes with Ki values in the μM to sub-μM range, and that this alkyl chain had to be longer or equal to a propyl chain. This result confirmed the importance of a carboxylic function on the 4-substituent of 1,2,4-triazole-3-thione heterocycle. As observed in previous series, active compounds also preferentially contained phenyl, 2-hydroxy-5-methoxyphenyl, naphth-2-yl or m-biphenyl at position 5. However, none efficiently inhibited NDM-1 or IMP-1. Microbiological study on VIM-2-producing E. coli strains and on VIM-1/VIM-4-producing multidrug-resistant K. pneumoniae clinical isolates gave promising results, suggesting that the 1,2,4-triazole-3-thione scaffold worth continuing exploration to further improve penetration. Finally, docking experiments were performed to study the binding mode of alkanoic analogues in the active site of VIM-2.

Benzothiazole compounds and medical application

The invention discloses a benzothiazole compound and medical application thereof, particularly relates to a benzothiazole compound shown as a formula I and medical application thereof, and especiallyrelates to application of the benzothiazole compound serving as a USP7C-terminal structural domain regulating agent in medicines for preventing and treating myelodysplastic syndromes and malignant tumors. The benzothiazole compound shown in the formula I or the pharmaceutically acceptable salt or solvate of the benzothiazole compound has strong binding force with USP7C-terminal protein; and the protein level of DNMT1 in tumor cells can be reduced, so that the compound can be applied to the preparation of USP7 regulators, has a remarkable anti-tumor cell proliferation effect, and can be used for preparing medicines for preventing or treating myelodysplastic syndrome and malignant tumors.

Anthracene derivative-based electroluminescent material as well as preparation method and application thereof

The invention discloses an electroluminescence material based on anthracene derivatives as well as a preparation method and application thereof. The electroluminescence material based on the anthracene derivatives is of a 7-membered condensed ring structure; better planarity is realized; the injection and the transmission of current carriers are facilitated; the photoelectric performance of the material is improved; through a fused ring structure, the anthracene derivatives have good rigidity; the heat-resistant capability of the material is favorably improved; the practical requirements of the material are met. Through Suzuki coupling reaction, Uhlmann coupling reaction, still coupling reaction and the like, the electroluminescence material based on anthracene derivatives is obtained; theelectroluminescence material has good dissolution performance; the common organic solvent dissolution is used; a film is formed through rotary coating, ink printing or printing film forming; a luminous layer of a light emitting diode is obtained through preparation.

IMIDE-CONTAINING LADDER TPYE HETEROARENES: SYNTHESIS AND RALATED ORGANIC SEMICONDUCTOR DEVICES

Small molecule and polymer semiconductors and their preparation methods are provided. These compounds are of formula I-III, and can be used in high-mobility organic thin-film transistors and bulk heterojunction polymer solar cells.

Continuous Flow Synthesis under High-Temperature/High-Pressure Conditions Using a Resistively Heated Flow Reactor

A cheap, easy-to-build, and effective resistively heated reactor for continuous flow synthesis at high temperature and pressure is herein presented. The reactor is rapidly heated directly using an electric current and is capable of rapidly delivering temperatures and pressures up to 400 °C and 200 bar, respectively. High-temperature and high-pressure applications of this reactor were safely performed and demonstrated by selected transformations such as esterifications, transesterifications, and direct carboxylic acid to nitrile reactions using supercritical ethanol, methanol, and acetonitrile. Reaction temperatures were between 300 and 400 °C with excellent conversions and good to excellent isolated product yields. Examples of Diels-Alder reactions were also carried out at temperatures up to 300 °C in high yield. No additives or catalysts were used in the reactions.

Ladder-type Heteroarenes: Up to 15 Rings with Five Imide Groups

A series of novel imide-functionalized ladder-type heteroarenes with well-defined structure and controllable conjugation lengths were synthesized and characterized. The synthetic route shows remarkable efficacy for constructing the electron-deficient ladder backbones. π-Conjugation extension leads to narrowed band gaps with enhanced electron affinities. The ladder arenes are incorporated into organic thin-film transistors, and show encouraging electron mobilities of 0.013–0.045 cm2 V?1 s?1. The heteroarenes reported here provide a remarkable platform for fundamental physicochemical studies and materials innovation in organic electronics.

Palladium-Catalyzed Carbonylations of Arylboronic Acids: Synthesis of Arylcarboxylic Acid Ethyl Esters

An approach for the palladium-catalyzed ethoxycarbonylations of arylboronic acids using diethyl pyrocarbonate as carbon monoxide/carbon dioxide (CO/CO2) surrogate in moderate to good yields has been investigated.

An unusual 1,2-aryl shift in palladium-catalyzed cross-coupling ethoxycarbonylation of arylboronic acids with α-iminoesters

The Pd-catalyzed cross-coupling ethoxycarbonylation of aryl boronic acids with N-aryl-α-iminoesters affords aryl carboxylic esters via carbonyl-imino σ bond cleavage. This unprecedented mode of reaction allows regioselective installation of the ethoxycarbonyl group into target molecules. Mechanism studies have revealed that an unusual 1,2-aryl shift process is involved in the transformation. The Royal Society of Chemistry.

Direct conversion of aromatic ketones to arenecarboxylic esters via carbon-carbon bond-cleavage reactions

Aromatic methyl ketones, ss-keto esters, and trifluoromethyl-l,3- diketones can be directly converted to arene-carboxylic esters via carbon-carbon bond cleavage of pyridinium iodide intermediates in the presence of copper(II) oxide, iodine, pyridine, and potassium carbonate in alcoholic media. The advantages of the present method in terms of good yields, mild reaction conditions, and inexpensive reagents should make this protocol a valuable alternative to the existing methods.

Palladium-catalyzed perarylation of 3-thiophene- and 3-furancarboxylic acids accompanied by C-H bond cleavage and decarboxylation

3-Thiophene- and 3-furancarboxylic acids efficiently undergo perarylation accompanied by cleavage of the three C-H bonds and decarboxylation upon treatment with excess aryl bromides in the presence of a palladium catalyst to give the corresponding tetraarylated products in good yields.