37784-63-7

Basic information

• Product Name: ETHYL THIOPHENE-3-ACETATE
• Synonyms: 3-Thiopheneacetic acid, ethyl ester;ETHYL 3-THIOPHENEACETATE;ETHYL 3-THIENYLACETATE;ETHYL THIOPHENE-3-ACETATE;thiophene-3-acetic acid ethyl ester;Ethyl 3-thiopheneacetate,98%;ethyl 2-(thiophen-3-yl)acetate
• CAS NO: 37784-63-7
• Molecular Formula: C₈H₁₀O₂S
• Molecular Weight: 170.23
• EINECS: 253-665-6
• Product Categories: Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Thiophenes
• Mol File: 37784-63-7.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 97 °C
• Flash Point: 103°C
• Appearance: Clear colorless to light brown/Liquid
• Density: 1.12
• Vapor Pressure: 0.0697mmHg at 25°C
• Refractive Index: 1.5090
• Storage Temp.: Refrigerator (+4°C)
• BRN: 122555
• CAS DataBase Reference: ETHYL THIOPHENE-3-ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL THIOPHENE-3-ACETATE(37784-63-7)
• EPA Substance Registry System: ETHYL THIOPHENE-3-ACETATE(37784-63-7)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 37784-63-7(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light brown liquid

Uses

Ethyl thiophene-3-acetate is used in the syntheses of poly(thiophene-3-acetic acid) and solution-processable polymers, which consist of polythiophene main chain and alkyl and oligoaniline side groups.

General Description

Ethyl 3-thiopheneacetate undergoes copolymerization with 3-alkylthiophene to yield poly(3-alkyl-2,5-thienylene-co-3-methyiene-ethylcarboxylate-2,5-thienylene).

InChI:InChI=1/C8H10O2S/c1-2-10-8(9)5-7-3-4-11-6-7/h3-4,6H,2,5H2,1H3

Upstream product

• 186581-53-3 diazomethane 
• 41507-35-1 3-thiophene carboxylic acid chloride 
• 13781-53-8 (thiophen-3-yl)acetonitrile 
• 64-17-5 ethanol 
• 95461-18-0 methyl 2,5-dichloro-3-thienylacetate 
• 32766-64-6 ethyl 2,5-dichloro-3-thienylglyoxylate 
• 872-31-1 3-Bromothiophene 
• 105-53-3 diethyl malonate 
• 71637-34-8 3-hydroxymethyl-thiophene 
• 95-92-1 oxalic acid diethyl ester 
• 905966-46-3 5,5-dimethyl-2-(thiophen-3-yl)-1,3,2-dioxaborinane 
• 1071-46-1 hydrogen ethyl malonate 
• 34967-61-8 2,5-dichlorothienylacetic acid 
• 21080-92-2 2-(thiophen-3-yl)malonic acid 

Downstream Products

• 37784-67-1 diethyl 2-(thiophen-3-yl)malonate 
• 6964-21-2 thiophen-3-yl-acetic acid 
• 175276-94-5 2-(thiophen-3-yl)acetohydrazide 
• 51536-25-5 ethyl 2-cyclohexyl-2-(3-thienyl)ethanoate 
• 1258516-37-8 methyl 3-(2-(2,5-di(thiophen-2-yl)thiophen-3-yl)-ethoxy)-5-(2-(5-(thiophen-2-yl)-2-(thiophen-3-yl)thiophen-3-yl)-ethoxy)benzoate 
• 1258289-16-5 (3-(2-(2,5-di(thiophen-2-yl)thiophen-3-yl)ethoxy)-5-(2-(5-(thiophen-2-yl)-2-(thiophen-3-yl)thiophen-3-yl)ethoxy)-phenyl)methanol 
• 1312573-74-2 ethyl 2-(4-(4-fluorophenyl)thiophen-3-yl)acetate 
• 1312573-72-0 ethyl 2-(4-(3-methoxyphenyl)thiophen-3-yl)acetate 
• 1312573-71-9 ethyl 2-(4-(o-tolyl)thiophen-3-yl)acetate 
• 1312573-73-1 ethyl 2-(4-(p-tolyl)thiophen-3-yl)acetate 
• 1312573-77-5 ethyl 2-(4-([1,1'-biphenyl]-4-yl)thiophen-3-yl)acetate 
• 1312573-70-8 ethyl 2-(4-phenylthiophen-3-yl)acetate 

Relevant articles and documents

Copper-Catalyzed Ullmann-Type Coupling and Decarboxylation Cascade of Arylhalides with Malonates to Access α-Aryl Esters

We have developed a high-efficiency and practical Cu-catalyzed cross-coupling to directly construct versatile α-aryl-esters by utilizing readily available aryl bromides (or chlorides) and malonates. These gram-scale approaches occur with turnovers of up to 1560 and are smoothly conducted by the usage of a low catalyst loading, a new available ligand, and a green solvent. A variety of functional groups are tolerated, and the application occurs with α-aryl-esters to access nonsteroidal anti-inflammatory drugs (NSAIDs) on the gram scale.

Ambient Decarboxylative Arylation of Malonate Half-Esters via Oxidative Catalysis

We report decarboxylative carbonyl α-arylation by coupling of arylboron nucleophiles with malonic acid derivatives. This process is enabled by the merger of aerobic oxidative Cu catalysis with decarboxylative enolate interception reminiscent of malonyl-CoA reactivity in polyketide biosynthesis. This method enables the synthesis of monoaryl acetate derivatives containing electrophilic functional groups that are incompatible with existing α-arylation reactivity paradigms. The utility of the reaction is demonstrated in drug intermediate synthesis and late-stage functionalization.

PROCESS FOR PREPARING ARYL- AND HETEROARYLACETIC ACID DERIVATIVES

The invention relates to a process for preparing aryl- and heteroarylacetic acids and derivatives thereof by reaction of aryl or heteroaryl halides with malonic diesters in the presence of a palladium catalyst, of one or more bases and optionally of a phase transfer catalyst. This process enables the preparation of a multitude of functionalized aryl- and heteroarylacetic acids and derivatives thereof, especially also the preparation of arylacetic acids with sterically demanding substituents.