Ethyl indole-5-carboxylate

Base Information

• Chemical Name: Ethyl indole-5-carboxylate
• CAS No.: 32996-16-0
• Molecular Formula: C11H11 N O2
• Molecular Weight: 189.214
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID90450838
• Nikkaji Number: J1.321.504I
• Wikidata: Q72475514
• Mol file: 32996-16-0.mol

Synonyms:Ethyl indole-5-carboxylate;32996-16-0;Ethyl 1H-indole-5-carboxylate;indole-5-carboxylic acid ethyl ester;1H-Indole-5-carboxylic acid, ethyl ester;1H-Indole-5-carboxylic acid ethyl ester;5-ethoxycarbonylindole;5-ethoxycarbonyl-1h-indole;poundAthyl indole-5-carboxylate;SCHEMBL1222893;DTXSID90450838;PDXPRWCJESNIIT-UHFFFAOYSA-N;BCP21406;MFCD01074506;AKOS006229575;AC-27789;AS-11394;Indole-5-carboxylic acid ethyl ester, 99%;A5894;CS-0037721;FT-0627225;I-2460;A821553

Chemical Property of Ethyl indole-5-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 96.5-97.5 °C
• Boiling Point: 342.357°C at 760 mmHg
• PKA: 16.09±0.30(Predicted)
• Flash Point: 160.852°C
• PSA: 42.09000
• Density: 1.211g/cm³
• LogP: 2.34460
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.9
• 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:

97% ^*data from raw suppliers

Indole-5-carboxylic acid ethyl ester ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=C(C=C1)NC=C2
• Uses: Ethyl Indole-5-carboxylate is used as a reagent in the synthesis of pyrazole-based cathepsin S inhibitors.

Technology Process of Ethyl indole-5-carboxylate

There total 10 articles about Ethyl indole-5-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: 98.0%

ethyl 4-amino-3-ethynylbenzoate (936840-07-2) → ethyl indole-5-carboxylate (32996-16-0)

Guidance literature:

With P(p-C₆H₄F)3; chloro(1,5-cyclooctadiene)rhodium(I) dimer; In N,N-dimethyl-formamide; at 85 ℃; for 2h;

DOI:10.1002/anie.200604183

Reference yield: 93.0%

1-(2,2-dimethyl-propionyl)-1H-indole-5-carboxylic acid ethyl ester → ethyl indole-5-carboxylate (32996-16-0)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; at 40 - 45 ℃; for 2h;

DOI:10.1055/s-2004-836060

Reference yield: 90.0%

1H-Indole-5-carboxylic acid (1670-81-1,142396-03-0) + ethanol (64-17-5) → ethyl indole-5-carboxylate (32996-16-0)

Guidance literature:

With thionyl chloride; for 2h; Reflux;

DOI:10.1016/j.bioorg.2019.02.048

upstream raw materials:

pyrano<4,3-b>pyrrol-6(1H)-one

propynoic acid ethyl ester

isobutyl 6-oxopyrano<4,3-b>pyrrole-1-carboxylate

5-bromo-1H-indole

Downstream raw materials:

ethyl 1-phenylsulfonylindole-5-carboxylate

1-benzoyl-1H-indole-5-carboxylic acid

1-acetyl-1H-indole-5-carboxylic acid

1H-indole-5-carbohydrazide