Ethyl indole-2-carboxylate

Base Information

• Chemical Name: Ethyl indole-2-carboxylate
• CAS No.: 3770-50-1
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.214
• Hs Code.: 29339990
• European Community (EC) Number: 223-206-4
• NSC Number: 10076
• UNII: WR9Y4AXI3Q
• DSSTox Substance ID: DTXSID60191140
• Nikkaji Number: J217.667J
• Wikidata: Q72475523
• ChEMBL ID: CHEMBL84245
• Mol file: 3770-50-1.mol

Synonyms:Ethyl indole-2-carboxylate;3770-50-1;Ethyl 1H-indole-2-carboxylate;Indole-2-carboxylic acid ethyl ester;2-Carbethoxyindole;1H-Indole-2-carboxylic acid, ethyl ester;Indole-2-carboxylic acid, ethyl ester;ETHYLINDOLE-2-CARBOXYLATE;MFCD00005609;1H-Indole-2-carboxylic acid ethyl ester;2-Ethoxycarbonylindole;NSC10076;WR9Y4AXI3Q;1H-INDOLE-2-CARBOXYLIC ACID,ETHYL ESTER;EINECS 223-206-4;NSC 10076;NSC-10076;ETHYL 2-INDOLECARBOXYLATE;2-carboethoxyindole;2-Carboethoxy-indole;ICA-OEt;ethyl-2-indolecarboxylate;Maybridge3_005325;UNII-WR9Y4AXI3Q;ethyl 2-indole carboxylate;ethyl-2-indole carboxylate;ethyl-indole-2-carboxylate;SCHEMBL42002;CHEMBL84245;DTXSID60191140;Ethyl indole-2-carboxylate, 97%;HMS1446C01;CS-D1745;indol-2-carboxylic acid ethyl ester;STR07814;CCG-15076;Indole 2-carboxylic acid ethyl ester;STK047851;2-Ethoxycarbonylindole, NSC 10076;AKOS000491241;AC-2541;CG-0521;SB14859;IDI1_016712;BP-12099;SY001911;AM20040324;BB 0254016;FT-0601210;I0585;EN300-25958;I-2400;AF-966/00545036;SR-01000388934;SR-01000388934-1;SR-01000388934-2;Z57205319

Chemical Property of Ethyl indole-2-carboxylate

Chemical Property:

• Appearance/Colour: white to yellow crystals or crystalline powder
• Vapor Pressure: 7.57E-05mmHg at 25°C
• Melting Point: 122-125 °C(lit.)
• Refractive Index: 1.62
• Boiling Point: 342.4 °C at 760 mmHg
• PKA: 15.01±0.30(Predicted)
• Flash Point: 160.9 °C
• PSA: 42.09000
• Density: 1.21 g/cm³
• LogP: 2.34460
• Storage Temp.: 0-6°C
• XLogP3: 3.2
• 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:

99% ^*data from raw suppliers

Indole-2-carboxylic acid ethyl ester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=CC=CC=C2N1
• Uses: Reactant for preparation of:? ;CRTH2 receptor antagonists1? ;Indoleamine 2,3-dioxygenase (IDO) inhibitors2? ;Cannabinoid CB1 receptor antagonists3? ;Inhibitors of Human Reticulocyte 15-Lipoxygenase-14? ;N-(benzoylphenyl)-1H-indole-2-carboxamides as potent antihypertriglyceridemic agents5? ;A antiproliferative agent against human leukemia K562 cells6? ;Inhibitors of p38 MAP kinase7? ;Acetolactate synthase inhibitors8 Reactant for preparation of:CRTH2 receptor antagonists;Indoleamine 2,3-dioxygenase (IDO) inhibitors;Cannabinoid CB1 receptor antagonists; Inhibitors of Human Reticulocyte 15-Lipoxygenase-1;N-(benzoylphenyl)-1H-indole-2-carboxamides as potent antihypertriglyceridemic agents;A antiproliferative agent against human leukemia K562 cells;Inhibitors of p38 MAP kinase; Acetolactate synthase inhibitors. 2-Ethoxycarbonylindole is a building block that has been used as a reactant for the preparation of pyridazinoindole derivatives that have antimicrobial activities.

Technology Process of Ethyl indole-2-carboxylate

There total 119 articles about Ethyl indole-2-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: 100.0%

Indole-2-carboxylic acid (1477-50-5,1228050-17-6) + ethanol (64-17-5) → 2-carbethoxyindole (3770-50-1,117770-52-2)

Guidance literature:

With hydrogenchloride; for 24h; Heating / reflux;

Reference yield: 99.0%

(S)-2,3-dihydro-1H-indole-2-carboxylic acid,ethyl ester (50501-07-0) → 2-carbethoxyindole (3770-50-1,117770-52-2)

Guidance literature:

With H₈O₂₀P₈Pt₂^(4-)*4C₃₄H₇₂N⁽¹⁺⁾; In methanol; Inert atmosphere; Irradiation;

DOI:10.1039/c8sc05600e

Reference yield: 98.0%

ethyl 2-nitrophenylpyruvate keto tautomer (784-98-5) → 2-carbethoxyindole (3770-50-1,117770-52-2)

Guidance literature:

With sodium dithionite; In 1,4-dioxane; water; for 3h; Reflux;

DOI:10.1016/j.tetlet.2018.09.039

upstream raw materials:

Indole-2-carboxylic acid

ethanol

2-ethoxycarbonyl-1-hydroxyindole

ethyl 2-nitrophenylpyruvate keto tautomer

Downstream raw materials:

ethyl 3-formyl-1H-indole-2-carboxylate

3-bromo-1H-indole-2-carboxylic acid ethyl ester

indole-2-carboxylic acid-(3,4-dimethoxy-phenethylamide)

ethyl 3-((dimethylamino)-methyl)-1H-indole-2-carboxylate

Refernces

• 1、 Al-Mutairi, Maha S.,Al-Wabli, Reem I.,Alsulami, Mona A.,Attia, Mohamed I.,Bukhari, Sarah I.,Moubayed, Nadine M. S.. "Design, synthesis, and antimicrobial activity of certain new indole-1,2,4 triazole conjugates". . . Retrieved 2021/05/28.
• 2、 Ahmed Fouad, Manar,Ferretti, Francesco,Formenti, Dario,Milani, Fabio,Ragaini, Fabio. "Synthesis of Indoles by Reductive Cyclization of Nitro Compounds Using Formate Esters as CO Surrogates". supporting information. p. 4876 - 4894. Retrieved 2021/09/20.