776-41-0

Basic information

• Product Name: Ethyl indole-3-carboxylate
• Synonyms: ETHYL INDOLE-3-CARBOXYLATE;INDOLE-3-CARBOXYLIC ACID ETHYL ESTER;1H-INDOLE-3-CARBOXYLIC ACID ETHYL ESTER;3-CARBETHOXYINDOLE;RARECHEM AL BI 0095;SPECS AN-068/14539028;INDOLE-3-CARBOXYLIC ACID ETHYL ESTER(I3CAEt);lindole-3-ethylforMate
• CAS NO: 776-41-0
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21
• EINECS: 1308068-626-2
• Product Categories: IndoleDerivative;Indole;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 776-41-0.mol
• Article Data: 24

Chemical Properties

• Melting Point: 120-124 °C
• Boiling Point: 342.4 °C at 760 mmHg
• Flash Point: 160.9 °C
• Appearance: /Solid
• Density: 1.21 g/cm₃
• Vapor Pressure: 7.57E-05mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: 2-8°C
• PKA: 15.42±0.30(Predicted)
• CAS DataBase Reference: Ethyl indole-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl indole-3-carboxylate(776-41-0)
• EPA Substance Registry System: Ethyl indole-3-carboxylate(776-41-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 776-41-0(Hazardous Substances Data)

Usage

Description

Ethyl indole-3-carboxylate is a yellow solid compound that has been isolated from the South China Sea sponge, Xetospongia testudinaria. It is known for its unique chemical properties and various applications across different industries.

Uses

Used in Pharmaceutical Industry:
Ethyl indole-3-carboxylate is used as a reactant for the preparation of indole-based heterocycles, which are essential in the synthesis of indole-based p38 inhibitors and gramines. These compounds play a crucial role in the development of new drugs for various medical applications.
Used in Neuroscience Research:
In the field of neuroscience, ethyl indole-3-carboxylate is used as a glycine receptor ligand. This application aids in the study of the nervous system and the development of treatments for neurological disorders.
Used in Inflammation and Allergy Research:
Ethyl indole-3-carboxylate is also used as an inhibitor of human 5-lipoxygenase, an enzyme involved in the production of leukotrienes, which are associated with inflammation and allergy. This application contributes to the development of anti-inflammatory and anti-allergic drugs.
Used in Antimicrobial Applications:
Furthermore, ethyl indole-3-carboxylate is utilized as an antimicrobial agent, demonstrating its potential in the development of new antibiotics and antifungal agents to combat drug-resistant infections.

InChI:InChI=1/C11H11NO2/c1-2-14-11(13)9-7-12-10-6-4-3-5-8(9)10/h3-7,12H,2H2,1H3

Upstream product

• 541-41-3 chloroformic acid ethyl ester 
• 623-73-4 diazoacetic acid ethyl ester 
• 529-23-7 o-aminobenzaldehyde 
• 140-88-5 ethyl acrylate 
• 942-24-5 3-methoxycarbonylindole 
• 98-95-3 nitrobenzene 
• 100-65-2 N-Phenylhydroxylamine 
• 623-47-2 propynoic acid ethyl ester 
• 95-14-7 1,2,3-Benzotriazole 
• 771-50-6 1H-indole-3-carboxylic acid 
• 64-17-5 ethanol 
• 7664-41-7 ammonia 
• 75-03-6 ethyl iodide 
• 22980-09-2 indolyl-3-glyoxylyl chloride 

Downstream Products

• 15317-58-5 1H-indole-3-carboxylic acid hydrazide 
• 91090-95-8 6-nitro-indole-3-carboxylic acid ethyl ester 
• 177200-90-7 N-Boc ethyl indole-3-carboxylate 
• 479595-34-1 2-(1H-indole-3-carbonyl)-N-(4-tolyl)hydrazinecarbothioamide 
• 891574-05-3 N-(4-chlorophenyl)-2-(1H-indole-3-carbonyl)hydrazinecarbothioamide 
• 436818-69-8 2-(1H-indole-3-carbonyl)-N-(4-methoxyphenyl)hydrazinecarbothioamide 
• 1396744-06-1 2-(1H-indole-3-carbonyl)-N-(4-(trifluoromethyl)phenyl)hydrazinecarbothioamide 
• 1396744-08-3 2-(1H-indole-3-carbonyl)-N-(3,4,5-trimethoxyphenyl)hydrazinecarbothioamide 
• 894231-58-4 2-(1H-indole-3-carbonyl)-N-(benzyl)hydrazinecarbothioamide 
• 894231-51-7 C₁₇H₁₆N₄OS 
• 891608-70-1 C₁₇H₁₅ClN₄OS 
• 1396744-12-9 C₂₃H₁₉ClN₄OS 
• 1396744-14-1 C₂₆H₂₅ClN₄O₄S 
• 1396744-16-3 N-[1-(4-methoxybenzyl)-1H-indol-3-ylcarbonyl]-N''-4-methoxyphenylthiosemicarbazide 

Relevant articles and documents

Convenient method of synthesizing 3-ethoxycarbonyl indoles

We have developed a convenient two-step procedure for the synthesis of 3-ethoxycarbonyl indoles from commercially available materials. The two-step procedure involves the synthesis of 2-aryl-3-hydroxypropenoic acid ester, followed by a catalytic reduction

A general and scalable synthesis of polysubstituted indoles

A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.

Catalytic synthesis method of indole compounds

The invention discloses a catalytic synthesis method of indole compounds.The method includes the following steps of firstly, conducting stirring reaction on ortho-nitrostyrolene or derivatives of ortho-nitrostyrolene, bis(pinacolato)diboron, alkali and low-grade saturated monohydric alcohol under the atmosphere of nitrogen; secondly, cooling the reaction product in the first step to the room temperature, adding ethyl acetate to be sufficiently mixed, and washing with ethyl acetate after filtering; thirdly, spin-drying low-grade saturated monohydric alcohol in an organic phase of the material obtained in the second step, passing through a silica gel column, and drip washing the silica gel column with eluent composed of petroleum ether and ethyl acetate to obtain pure products, namely, the indole compounds.By means of the method, under the neutral conditions, bis(pinacolato)diboron low in price serves as the raw material, friendly low-grade saturated monohydric alcohol serves as the solvent, the indole compounds are obtained through simple operation, the raw materials are low in price and easy to obtain, efficiency and safety are high, and wide expandability and good industrial application prospects are achieved.