Methyl 5-methyl-1H-indole-2-carboxylate

Base Information

• Chemical Name: Methyl 5-methyl-1H-indole-2-carboxylate
• CAS No.: 102870-03-1
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.21100
• DSSTox Substance ID: DTXSID70406439
• Wikidata: Q82211394
• Mol file: 102870-03-1.mol

Synonyms:Methyl 5-methyl-1H-indole-2-carboxylate;102870-03-1;1H-Indole-2-carboxylic acid, 5-methyl-, methyl ester;5-Methylindole-2-carboxylic acid methyl ester;methyl 5-methylindole-2-carboxylate;SCHEMBL214096;DTXSID70406439;WMYBSXNKEVGXGX-UHFFFAOYSA-N;CEA87003;LH0050;MFCD07364546;AKOS004117234;Methyl5-methyl-1H-indole-2-carboxylate;BS-51448;CS-0160702;FT-0750556;D83698;A896689

Chemical Property of Methyl 5-methyl-1H-indole-2-carboxylate

Chemical Property:

• Boiling Point: 345.1±22.0 °C(Predicted)
• PKA: 15.14±0.30(Predicted)
• PSA: 42.09000
• Density: 1.212±0.06 g/cm3(Predicted)
• LogP: 2.26290
• Storage Temp.: 2-8°C
• XLogP3: 2.8
• 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

Methyl5-methyl-1H-indole-2-carboxylate 97% ^*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(=C2)C(=O)OC

Technology Process of Methyl 5-methyl-1H-indole-2-carboxylate

There total 7 articles about Methyl 5-methyl-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: 65.0%

(Z)-methyl 3-(dimethylamino)-2-[(4-methylphenyl)amino]acrylate (888723-76-0) → 5-methylindole-2-carboxylic acid methyl ester (102870-03-1)

Guidance literature:

With aluminium trichloride; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1055/s-2006-933135

Reference yield:

5-methylindole-2-carboxylic acid (10241-97-1) → 5-methylindole-2-carboxylic acid methyl ester (102870-03-1)

Guidance literature:

With sodium bicarbonate; sulfuric acid; In methanol;

Reference yield:

methanol (67-56-1) + 5-methylindole-2-carboxylic acid (10241-97-1) → 5-methylindole-2-carboxylic acid methyl ester (102870-03-1)

Guidance literature:

With hydrogenchloride; at 20 ℃;

DOI:10.1021/jm0490540

upstream raw materials:

methanol

5-methylindole-2-carboxylic acid

(Z)-methyl 3-(dimethylamino)-2-[(4-methylphenyl)amino]acrylate

methyl 2-(4-methylphenylamino)acetate

Downstream raw materials:

2-(allyloxymethyl)-1-benzyl-5-methyl-1H-indole

(E)-4-((1-benzyl-5-methyl-1H-indol-2-yl)methoxy)but-2-enal

Methyl 1-cyanomethyl-5-methyl-1H-indole-2-carboxylate

1,5-dimethyl-1H-indole-2-carbaldehyde

Refernces

• 1、 Jerezano, Alberto V.,Labarrios, Ehecatl M.,Jimenez, Fabiola E.,Del Cruz, Maria Carmen,Pazos, Diana C.,Gutierrez, Rsuini U.,Delgado, Francisco,Tamariz, Joaquin. "Iodine-mediated one-pot synthesis of indoles and 3-dimethylaminoindoles via annulation of enaminones". . p. 18 - 53. Retrieved 2014/03/21.
• 2、 Cruz, María Del Carmen,Jiménez, Fabiola,Delgado, Francisco,Tamariz, Joaquín. "Regioselective and versatile synthesis of indoles via intramolecular Friedel-Crafts heteroannulation of enaminones". . p. 749 - 755. Retrieved 2007/10/03.