methyl 5-methyl-1H-indole-3-carboxylate

Base Information

• Chemical Name: methyl 5-methyl-1H-indole-3-carboxylate
• CAS No.: 227960-12-5
• Molecular Formula: C11H11 N O2
• Molecular Weight: 189.214
• Hs Code.: 2933990090
• European Community (EC) Number: 672-336-1
• DSSTox Substance ID: DTXSID80374953
• Nikkaji Number: J1.932.322F
• Wikidata: Q72492865
• ChEMBL ID: CHEMBL4863910
• Mol file: 227960-12-5.mol

Synonyms:227960-12-5;Methyl 5-methylindole-3-carboxylate;methyl 5-methyl-1H-indole-3-carboxylate;5-Methylindole-3-carboxylic acid methyl ester;5-Methyl-1H-indole-3-carboxylic acid methyl ester;CHEMBL4863910;MFCD02179412;SCHEMBL4240354;AMY2817;DTXSID80374953;ZECAAQDHFZNFPB-UHFFFAOYSA-N;Methyl5-methylindole-3-carboxylate;BDBM50577594;3-methoxycarbonyl-5-methyl-1H-indole;AKOS006345220;AC-6493;SB35611;AS-62149;SY058800;A4853;CS-0148297;FT-0630303;5-methylindole-3-carboxylic acid methyl ester, AldrichCPR

Chemical Property of methyl 5-methyl-1H-indole-3-carboxylate

Chemical Property:

• Vapor Pressure: 6.28E-05mmHg at 25°C
• Boiling Point: 345.1°Cat760mmHg
• PKA: 15.59±0.30(Predicted)
• Flash Point: 162.5°C
• PSA: 42.09000
• Density: 1.212g/cm³
• LogP: 2.26290
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 189.078978594
• Heavy Atom Count: 14
• Complexity: 229

Purity/Quality:

98%min ^*data from raw suppliers

5-Methylindole-3-carboxylicacidmethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)NC=C2C(=O)OC

Technology Process of methyl 5-methyl-1H-indole-3-carboxylate

There total 3 articles about methyl 5-methyl-1H-indole-3-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: 77.0%

N-(4-methylphenyl)hydroxylamine (623-10-9) + propynoic acid methyl ester (922-67-8) → methyl 5-methyl-1H-indole-3-carboxylate (227960-12-5)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; In dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.3390/molecules25235595

Reference yield: 17.0%

methyl 1-(4-methylphenyl)-1H-1,2,3-triazole-4-carboxylate (227959-99-1) → methyl N-(4-methylphenyl)ketenimine-2-carboxylate (227960-01-2) + methyl 5-methyl-1H-indole-3-carboxylate (227960-12-5) + 2-methoxy-6-methylquinolin-4-one

Guidance literature:

at 500 ℃; for 2h;

DOI:10.1021/jo982471y

Reference yield:

C24H19NO3 → 9-fluorenone (486-25-9,952573-42-1) + methyl 5-methyl-1H-indole-3-carboxylate (227960-12-5)

Guidance literature:

With oxalic acid adsorbed on silica gel; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1055/s-0035-1560210

upstream raw materials:

methyl 1-(4-methylphenyl)-1H-1,2,3-triazole-4-carboxylate

N-(4-methylphenyl)hydroxylamine

propynoic acid methyl ester

Downstream raw materials:

5-methyl-1H-indole-3-carboxylic acid

3-(4-{[1-(3,4-Dimethyl-benzyl)-5-methyl-1H-indole-3-carbonyl]-amino}-benzylamino)-propionic acid

1-(3,4-dimethylbenzyl)-N-(4-formylphenyl)-5-methyl-1H-indole-3-carboxamide

1-(3,4-dimethylbenzyl)-N[4-(hydroxymethyl)phenyl]-5-methyl-1H-indole-3-carboxamide

Refernces

• 1、 Natarajan, Rakesh,Rappai, John P.,Unnikrishnan, Peruparampil A.,Radhamani, Sandhya,Prathapan, Sreedharan. "A New Method for the Synthesis of 3-Substituted Indoles". supporting information. p. 2467 - 2471. Retrieved 2015/10/19.