3199-61-9

Basic information

• Product Name: 2-BENZOFURANCARBOXYLIC ACID, ETHYL ESTER
• Synonyms: RARECHEM AL BI 0556;2-BENZOFURANCARBOXYLIC ACID, ETHYL ESTER;BENZOFURAN-2-CARBOXYLIC ACID ETHYL ESTER;BENZOFURAN-2-CARBOXLIC ACID ETHYL ESTER;Ethyl benzo[b]furan-2-carboxylate 97%;7-Bromo-4-fluorobenzofuran;Ethyl 1-benzofuran-2-carboxylate;ethyl benzofuran-2-carboxylate
• CAS NO: 3199-61-9
• Molecular Formula: C₁₁H₁₀O₃
• Molecular Weight: 190.2
• Product Categories: Miscellaneous
• Mol File: 3199-61-9.mol
• Article Data: 60

Chemical Properties

• Melting Point: 166-170℃
• Boiling Point: 105°/0.1mm
• Flash Point: >110℃
• Appearance: /
• Density: 1.1656
• Vapor Pressure: 0.00554mmHg at 25°C
• Refractive Index: 1.5640 (estimate)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-BENZOFURANCARBOXYLIC ACID, ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BENZOFURANCARBOXYLIC ACID, ETHYL ESTER(3199-61-9)
• EPA Substance Registry System: 2-BENZOFURANCARBOXYLIC ACID, ETHYL ESTER(3199-61-9)

Safety Data

• Hazard Codes: T
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 3199-61-9(Hazardous Substances Data)

Usage

Uses

Ethyl Coumarilate has been used as a reactant for the preparation of benzofuropyridines that have a high affinity for the α2-adrenoceptor.

Preparation

Synthesis of ethyl benzofuran-2-carboxylate: Salicylaldehyde (20.0 mL, 0.164 mol) and diethyl bromomalonate (40.0 mL, 0.168 mol) in ethyl methyl ketone (40.0 mL, 0.555 mol) was treated with anhydrous potassium carbonate (20.0 g,0.869 mol). The reaction mixture was refluxed for 18 h on steam bath. Ethyl methyl ketone was distilled off under reduced pressure and the residue formed was dissolved in 400 mL of water and cooled in an ice-bath. It was acidified with dil H2SO4. The product formed was extracted with 25 mL portion of solvent ether twice and the extract was washed with sodium bicarbonate solution. It was dried over calcium chloride. Solvent was removed and the residue ethyl benzofuran-2-carboxylate was dried.

InChI:InChI=1/C11H10O3/c1-2-13-11(12)10-7-8-5-3-4-6-9(8)14-10/h3-7H,2H2,1H3

Upstream product

• 271-89-6 1-benzofurane 
• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 32865-61-5 2-iodophenyl acetate 
• 623-47-2 propynoic acid ethyl ester 
• 90-02-8 salicylaldehyde 
• 105-39-5 chloroacetic acid ethyl ester 
• 496-41-3 Benzofuran-2-carboxylic acid 
• 75-03-6 ethyl iodide 
• 91703-34-3 2-(β,β-dibromovinyl)phenol 
• 13939-06-5 molybdenum hexacarbonyl 
• 54008-77-4 2-bromo-1-benzofuran 
• 89-95-2 2-methyl-benzyl alcohol 
• 105-36-2 ethyl bromoacetate 

Downstream Products

• 78917-44-9 2-Benzofuranpropionic acid-β-oxo-ethylester 
• 496-41-3 Benzofuran-2-carboxylic acid 
• 42974-19-6 benzo[b]furan-2-carbohydrazide 
• 50342-50-2 benzofuran-2-carboxamide 
• 3199-62-0 α,α-diphenyl-2-benzofuranmethanol 
• 50635-12-6 benzofuran-2-carboxylic acid N-phenylamide 
• 41014-27-1 2-bromomethylbenzofuran 
• 112521-75-2 5-(benzofuran-2-yl)-1,3,4-oxadiazole-2-thiol 
• 307002-71-7 CL-82198 

Relevant articles and documents

Benzofuran hydrazones as potential scaffold in the development of multifunctional drugs: Synthesis and evaluation of antioxidant, photoprotective and antiproliferative activity

New benzofuranhydrazones 3–12 were easily prepared and assayed for their radical-scavenging ability. Hydrazones 3–12 showed different extent antioxidant activity in DPPH, FRAP and ORAC assays. Good antioxidant activity is related to the number and positio

P(MeNCH2CH2)3N: An efficient catalyst for the synthesis of substituted ethyl benzofuran-2-carboxylates

A superior method for the synthesis of substituted ethyl benzofuran-2-carboxylates in 80-99% yields from substituted 2-formylphenoxy ethylcarboxylates using 0.4 equiv of commercially available P(MeNCH2CH2)3N at 70 °C for 3 hours is described.

Microwave induced thermal gradients in solventless reaction systems

Development of thermal heterogeneity under microwave irradiation for solventless solid-liquid phase-transfer catalytic (PTC) reactions has been studied by means of a thermovision camera and fiber-optics thermometer.

Synthesis and biological evaluation of a series of novel benzofuran-2-carboxylate 1,2,3-triazoles

A facile and efficient synthetic route has been developed to substituted benzofuran-2-carboxylate 1,2,3-triazoles for the first time by reacting prop-2-yn-1-yl benzofuran-2-carboxylate with a variety of substituted aryl/benzyl azides in DMF/H2O system employing standard click reaction. This new method has the lead of good yields, inexpensive reagents, easily available, easy work-up, mild reaction conditions, and environmentally friendly reaction conditions. All these compounds have been characterized by modern spectral techniques such as IR, 1H NMR, and mass spectroscopy, etc. Evaluation of synthesized compounds for antimicrobial activity against specific bacterial strains like Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa along with antifungal activity against Aspergillus Niger and Sclerotium rolfsii have been carried out.

Synthesis, α-glucosidase inhibition, and molecular docking studies of novel N-substituted hydrazide derivatives of atranorin as antidiabetic agents

A series of novel N-substituted hydrazide derivatives were synthesized by reacting atranorin, a compound with a natural depside structure (1), with a range of hydrazines. The natural product and 12 new analogues (2–13) were investigated for inhibition of α-glucosidase. The N-substituted hydrazide derivatives showed more potent inhibition than the original. The experimental results were confirmed by docking analysis. This study suggests that these compounds are promising molecules for diabetes therapy. Molecular dynamics simulations were carried out with compound 2 demonstrating the best docking model using Gromac during simulation up to 20 ns to explore the stability of the complex ligand-protein. Furthermore, the activity of all synthetic compounds 2–13 against a normal cell line HEK293, used for assessing their cytotoxicity, was evaluated.