Ethyl 5-methoxyindole-2-carboxylate

Base Information

• Chemical Name: Ethyl 5-methoxyindole-2-carboxylate
• CAS No.: 4792-58-9
• Molecular Formula: C12H13NO3
• Molecular Weight: 219.24
• Hs Code.: 2933990090
• NSC Number: 30929
• UNII: D63U367GNZ
• DSSTox Substance ID: DTXSID30197351
• Nikkaji Number: J26.043F
• Wikidata: Q27276153
• ChEMBL ID: CHEMBL1366214
• Mol file: 4792-58-9.mol

Synonyms:4792-58-9;Ethyl 5-methoxyindole-2-carboxylate;ethyl 5-methoxy-1H-indole-2-carboxylate;5-Methoxyindole-2-carboxylic acid ethyl ester;1H-Indole-2-carboxylic acid, 5-methoxy-, ethyl ester;Ethyl5-methoxyindole-2-carboxylate;5-methoxy-1H-indole-2-carboxylic acid ethyl ester;Ethyl 5-methoxy-2-indolecarboxylate;MFCD00047163;NSC 30929;BRN 0178104;UNII-D63U367GNZ;Methoxy-5 indole carboxylate d'ethyle-2;MLS000071430;D63U367GNZ;INDOLE-2-CARBOXYLIC ACID, 5-METHOXY-, ETHYL ESTER;Methoxy-5 indole carboxylate d'ethyle-2 [French];NSC-30929;SMR000038189;5-22-05-00181 (Beilstein Handbook Reference);NSC30929;5-METHOXY-2-CARBETHOXYINDOLE;5-MeO-ICA-OEt;5-methoxyindole-2-carboxylic acid*ethyl ester;Oprea1_242778;SCHEMBL75327;2-carbethoxy-5-methoxyindole;cid_20926;CHEMBL1366214;BDBM39434;DTXSID30197351;HMS2278K12;BBL012858;STK501706;ethyl 5-methoxy-indole-2-carboxylate;AKOS000264906;CS-W014763;NCGC00018444-01;NCGC00018444-02;DS-14883;LS-82722;SY078933;5-methoxy-indole-2-carboxylicaciethylester;BB 0256844;FT-0626128;EN300-160218;M-3504;5-Methoxy Indole-2-Carboxylic Acid Ethyl ester;A827393;Q27276153;5-Methoxyindole-2-carboxylic acid ethyl ester, crystalline

Chemical Property of Ethyl 5-methoxyindole-2-carboxylate

Chemical Property:

• Appearance/Colour: yellow solid
• Vapor Pressure: 5.54E-06mmHg at 25°C
• Melting Point: 154-157°C
• Refractive Index: 1.599
• Boiling Point: 380.2 °C at 760 mmHg
• PKA: 14.72±0.30(Predicted)
• Flash Point: 183.7 °C
• PSA: 51.32000
• Density: 1.216 g/cm³
• LogP: 2.35320
• Storage Temp.: −20°C
• Water Solubility.: Insoluble in water.
• 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:

95% ^*data from raw suppliers

Ethyl5-Methoxy-1H-indole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=C(N1)C=CC(=C2)OC
• Uses: It is reactant for preparation of ligands with binding specificity towards the GABA receptor, sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors for the management of hyperglycemia in diabetes, anticancer agents,integrase strand-transfer inhibitors (INSTIs),inhibitor of Proliferation of Colon Cancer Cells ,isomeridianin G as GSK-3? inhibitors, HIV-1 integrase inhibitors and inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2).

Technology Process of Ethyl 5-methoxyindole-2-carboxylate

There total 31 articles about Ethyl 5-methoxyindole-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: 99.0%

5-methoxy-1H-indole-2-carboxylic acid (4382-54-1) + ethanol (64-17-5) → ethyl 5-methoxy-1H-indole-2-carboxylate (4792-58-9)

Guidance literature:

With sulfuric acid; for 10h; Reflux;

DOI:10.1016/j.tet.2013.01.090

Reference yield: 98.0%

5-methoxy-1H-indole-2-carboxylic acid (4382-54-1) → ethyl 5-methoxy-1H-indole-2-carboxylate (4792-58-9)

Guidance literature:

With sulfuric acid;

Reference yield: 91.0%

2-oxo-propionic acid ethyl ester (617-35-6) + 4-methoxy-aniline (104-94-9) → ethyl 5-methoxy-1H-indole-2-carboxylate (4792-58-9)

Guidance literature:

With oxygen; palladium diacetate; acetic acid; In dimethyl sulfoxide; at 70 ℃; for 18h; Temperature; Reagent/catalyst; Schlenk technique; Molecular sieve;

upstream raw materials:

ethyl 2-[2-(4-methoxyphenyl)hydrazinylidene]propanoate

5-methoxy-1H-indole-2-carboxylic acid

ethanol

5-methoxy-1-phenylmethyl-1H-indole-2-carboxylic acid,ethyl ester

Downstream raw materials:

1-(2-dibenzylaminoethyl)-5-methoxy-2-ethoxycarbonylindole

5-methoxy-1-phenylmethyl-1H-indole-2-carboxylic acid,ethyl ester

3-formyl-5-methoxy-indole-2-carboxylic acid ethyl ester

2-Carbethoxy-3-phenylazo-5-methoxyindole