Ethyl indole-3-carboxylate

Base Information

• Chemical Name: Ethyl indole-3-carboxylate
• CAS No.: 776-41-0
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.214
• Hs Code.: 2933998090
• European Community (EC) Number: 805-824-1
• NSC Number: 63796
• UNII: UEW9VF3T3M
• DSSTox Substance ID: DTXSID70289769
• Nikkaji Number: J291.454I
• Wikidata: Q72475509
• ChEMBL ID: CHEMBL4855970
• Mol file: 776-41-0.mol

Synonyms:Indole-3-carboxylicacid, ethyl ester (6CI,7CI,8CI);Ethyl 1H-indole-3-carboxylate;Ethylindole-3-carboxylate;NSC 63796;

Chemical Property of Ethyl indole-3-carboxylate

Chemical Property:

• Appearance/Colour: yellowy Solid
• Vapor Pressure: 7.57E-05mmHg at 25°C
• Melting Point: 120-124 °C
• Refractive Index: 1.62
• Boiling Point: 342.4 °C at 760 mmHg
• PKA: 15.42±0.30(Predicted)
• Flash Point: 160.9 °C
• PSA: 42.09000
• Density: 1.21 g/cm₃
• LogP: 2.34460
• Storage Temp.: 2-8°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 189.078978594
• Heavy Atom Count: 14
• Complexity: 217

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl Indole-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CNC2=CC=CC=C21
• Uses: Ethyl Indole-3-carboxylate is a compound that has been isolated from the south China sea sponge, Xetospongia testudinaria. Reactant for preparation of:Indole-based heterocycles for synthesis of indole-based p38 inhibitors and graminesGlycine receptor ligandsInhibitors of Human 5-LipoxygenaseAntimicrobial agents

Technology Process of Ethyl indole-3-carboxylate

There total 40 articles about Ethyl indole-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

(E)-3-(2-Bromo-phenylamino)-acrylic acid ethyl ester → indole-3-carboxylic acid ethyl ester (776-41-0)

Guidance literature:

With triethylamine; palladium diacetate; tris-(o-tolyl)phosphine; In acetonitrile; at 100 ℃; for 20h;

DOI:10.1246/bcsj.59.927

Reference yield: 90.0%

ethyl 3-hydroxy-2-(2-nitrophenyl)propenoate → indole-3-carboxylic acid ethyl ester (776-41-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 24h; under 2280 Torr;

DOI:10.1021/jo0601821

Reference yield: 88.0%

ethanol (64-17-5) + 2,2,2-trichloro-1-(1H-indol-3-yl)ethan-1-one (30030-90-1) → indole-3-carboxylic acid ethyl ester (776-41-0)

Guidance literature:

With potassium hydroxide; for 0.5h; Heating;

upstream raw materials:

Indole-3-carbonyl chloride

chloroformic acid ethyl ester

ethanol

2,2,2-trichloro-1-(1H-indol-3-yl)ethan-1-one

Downstream raw materials:

1-Benzoylindol-3-carbonsaeureethylester

1-Carbobenzoxyindol-3-carbonsaeureethylester

1-(3,5-Dinitrobenzoyl)-indol-3-carbonsaeureethylester

N-Boc ethyl indole-3-carboxylate

Refernces

• 1、 Zaienne, Daniel,Willems, Sabine,Schierle, Simone,Heering, Jan,Merk, Daniel. "Development and Profiling of Inverse Agonist Tools for the Neuroprotective Transcription Factor Nurr1". . p. 15126 - 15140. Retrieved 2021/10/25.
• 2、 Abe, Takumi,Yamada, Koji. "Amination/Cyclization Cascade by Acid-Catalyzed Activation of Indolenine for the One-Pot Synthesis of Phaitanthrin E". supporting information. p. 6504 - 6507. Retrieved 2016/12/23.