Ethyl 6-methoxy-1H-indole-2-carboxylate

Base Information

• Chemical Name: Ethyl 6-methoxy-1H-indole-2-carboxylate
• CAS No.: 15050-04-1
• Molecular Formula: C12H13 N O3
• Molecular Weight: 219.24
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID80346514
• Nikkaji Number: J102.707G
• Wikidata: Q82119609
• Mol file: 15050-04-1.mol

Synonyms:Ethyl 6-methoxy-1H-indole-2-carboxylate;15050-04-1;6-Methoxy-1H-indole-2-carboxylic acid ethyl ester;ethyl 6-methoxyindole-2-carboxylate;1H-Indole-2-carboxylic acid, 6-methoxy-, ethyl ester;Indole-2-carboxylic acid, 6-methoxy-, ethyl ester;MFCD01544121;Ethyl6-methoxy-1H-indole-2-carboxylate;Oprea1_681677;6-METHOXYINDOLE-2-CARBOXYLIC ACID ETHYL ESTER;SCHEMBL1319990;DTXSID80346514;Ethyl 6-methoxy-2-indolecarboxylate;LH0047;AKOS005174370;LS-04473;Ethyl 6-methoxy-1H-indole-2-carboxylate #;BB 0262633;CS-0103593;EN300-56916;J-518831;Z293535818

Chemical Property of Ethyl 6-methoxy-1H-indole-2-carboxylate

Chemical Property:

• Vapor Pressure: 5.54E-06mmHg at 25°C
• Melting Point: 135-136 °C
• Boiling Point: 380.2oC at 760 mmHg
• PKA: 15.24±0.30(Predicted)
• Flash Point: 183.7oC
• PSA: 51.32000
• Density: 1.216g/cm3
• LogP: 2.35320
• Storage Temp.: 2-8°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 219.08954328
• Heavy Atom Count: 16
• Complexity: 257

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl 6-methoxy-1H-indole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=C(N1)C=C(C=C2)OC

Technology Process of Ethyl 6-methoxy-1H-indole-2-carboxylate

There total 20 articles about Ethyl 6-methoxy-1H-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: 85.0%

2-(4-methoxy-2-nitrophenyl)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)ethan-1-one → 6-methoxy-1H-indole-2-carboxylic acid ethyl ester (15050-04-1)

Guidance literature:

2-(4-methoxy-2-nitrophenyl)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)ethan-1-one; With titanium(III) chloride; ammonium acetate; In ethanol; water; at 20 ℃; for 1h; Inert atmosphere;

With toluene-4-sulfonic acid; In ethanol; at 115 ℃; for 16h;

DOI:10.1021/acs.orglett.8b01614

Reference yield: 81.0%

2-oxo-propionic acid ethyl ester (617-35-6) + m-Anisidine (536-90-3,918666-97-4) → 6-methoxy-1H-indole-2-carboxylic acid ethyl ester (15050-04-1) + ethyl 4-methoxy-indole-2-carboxylate (43142-25-2)

Guidance literature:

With oxygen; palladium diacetate; acetic acid; In dimethyl sulfoxide; at 70 ℃; for 18h; under 760.051 Torr; Schlenk technique; Molecular sieve;

DOI:10.1021/acs.joc.8b02180

Reference yield: 75.0%

2-oxo-propionic acid ethyl ester (617-35-6) + m-Anisidine (536-90-3,918666-97-4) → 6-methoxy-1H-indole-2-carboxylic acid ethyl ester (15050-04-1)

Guidance literature:

With oxygen; palladium diacetate; acetic acid; In dimethyl sulfoxide; at 70 ℃; for 18h; under 760.051 Torr; regioselective reaction; Schlenk technique; Molecular sieve;

DOI:10.1021/acs.joc.8b02180

upstream raw materials:

6-Methoxyindole-2-carboxylic acid

ethanol

ethyl 2-((3-methoxyphenyl)amino)acetate

m-Anisidine

Downstream raw materials:

6-Methoxyindole-2-carboxylic acid

C₁₆H₁₅NO₂

C₁₆H₁₄FNO₂

Refernces

• 1、 -. "AROMATIC RING DERIVATIVE AS IMMUNOREGULATION AND PREPARATION METHOD AND APPLICATION OF AROMATIC RING DERIVATIVE". . . Retrieved 2021/10/15.
• 2、 Preti, Delia,Romagnoli, Romeo,Rondanin, Riccardo,Cacciari, Barbara,Hamel, Ernest,Balzarini, Jan,Liekens, Sandra,Schols, Dominique,Estévez-Sarmiento, Francisco,Quintana, José,Estévez, Francisco. "Design, synthesis, in vitro antiproliferative activity and apoptosis-inducing studies of 1-(3′,4′,5′-trimethoxyphenyl)-3-(2′-alkoxycarbonylindolyl)-2-propen-1-one derivatives obtained by a molecular hybridisation approach". . p. 1225 - 1238. Retrieved 2018/09/04.