Methyl indole-6-carboxylate

Base Information

• Chemical Name: Methyl indole-6-carboxylate
• CAS No.: 50820-65-0
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Hs Code.: 29339900
• European Community (EC) Number: 610-576-0
• DSSTox Substance ID: DTXSID80348674
• Nikkaji Number: J258.259G
• Wikidata: Q72491922
• ChEMBL ID: CHEMBL4212523
• Mol file: 50820-65-0.mol

Synonyms:Methyl indole-6-carboxylate;50820-65-0;methyl 1H-indole-6-carboxylate;Indole-6-carboxylic acid methyl ester;1H-indole-6-carboxylic acid, methyl ester;MFCD00211063;methylindole-6-carboxylate;1H-indole-6-carboxylic acid methyl ester;Indole-7-carboxylate;6-carbomethoxyindole;Indole-6-carboxylate;6-methoxycarbonylindole;5-Chloro-7-hydroxyindole;methyl 6-indolecarboxylate;methyl indole-6carboxylate;methyl-6-indolecarboxylate;methyl-indole-6-caroxylate;methyl-indole-6-carboxylate;SCHEMBL145507;Methyl-(indol-6-yl)methanoate;CHEMBL4212523;BDBM93021;DTXSID80348674;Methyl indole-6-carboxylate, 97%;BCP26492;STK500478;AKOS000321406;AC-1393;CS-W017455;FS-1436;PB18468;SY002751;AM20040584;FT-0628740;M2042;A16067;EN300-184462;I-2520;Q-102578;Z418671152

Chemical Property of Methyl indole-6-carboxylate

Chemical Property:

• Appearance/Colour: Off-white crystalline powder
• Vapor Pressure: 0.000153mmHg at 25°C
• Melting Point: 76-80 °C(lit.)
• Refractive Index: 1.639
• Boiling Point: 331.7 °C at 760 mmHg
• PKA: 15.80±0.30(Predicted)
• Flash Point: 154.4 °C
• PSA: 42.09000
• Density: 1.253 g/cm³
• LogP: 1.95450
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Chloroform, Methanol
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 175.063328530
• Heavy Atom Count: 13
• Complexity: 205

Purity/Quality:

99% ^*data from raw suppliers

Methyl indole-6-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC2=C(C=C1)C=CN2
• Uses: An indole compound for treating pain, inflammation and other conditions.

Technology Process of Methyl indole-6-carboxylate

There total 27 articles about Methyl indole-6-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: 92.0%

2-ethynyl-5-(methoxycarbonyl)aniline → indole-6-carboxylic acid methyl ester (50820-65-0)

Guidance literature:

With chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II); In pyridine; at 90 ℃; for 1.5h; regioselective reaction; Inert atmosphere;

DOI:10.1002/adsc.201100095

Reference yield: 91.9%

methanol (67-56-1) + Indole-6-carboxylic acid (1670-82-2,261352-47-0) → indole-6-carboxylic acid methyl ester (50820-65-0)

Guidance literature:

With sulfuric acid; at 70 ℃; for 15h;

Reference yield: 87.0%

Indole-6-carboxylic acid (1670-82-2,261352-47-0) + methyl iodide (74-88-4) → indole-6-carboxylic acid methyl ester (50820-65-0)

Guidance literature:

Indole-6-carboxylic acid; With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

methyl iodide; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

upstream raw materials:

indole-3,6-dicarboxylic acid-6-methyl ester

1-ethenyl-2-pyrrolidinone

2-bromo-5-methoxycarbonylaniline

2-<(4-methoxycarbonyl-2-nitrophenyl)methyl>-1,3-dioxane

Downstream raw materials:

Indole-6-carboxylic acid

6-(hydroxymethyl)indole

C₂₄H₂₁NO₄S

1-(3,5-difluoro-benzyl)-1H-indole-6-carboxylic acid methyl ester

Refernces

• 1、 -. "A method of synthesis of indole derivatives". Paragraph 0018-0021. . Retrieved 2022/01/10.
• 2、 -. "HEPARANASE INHIBITORS AND USE THEREOF". Paragraph 0176. . Retrieved 2018/07/05.