Ethyl 5-methylindole-2-carboxylate

Base Information

• Chemical Name: Ethyl 5-methylindole-2-carboxylate
• CAS No.: 16382-15-3
• Molecular Formula: C12H13NO2
• Molecular Weight: 203.241
• Hs Code.: 2933990090
• NSC Number: 30928
• DSSTox Substance ID: DTXSID50283326
• Nikkaji Number: J769.700G
• Wikidata: Q72475985
• ChEMBL ID: CHEMBL1518533
• Mol file: 16382-15-3.mol

Synonyms:Ethyl 5-methylindole-2-carboxylate;16382-15-3;ethyl 5-methyl-1H-indole-2-carboxylate;2-CARBETHOXY-5-METHYLINDOLE;MFCD00022703;NSC30928;5-Methylindole-2-carboxylic acid ethyl ester;5-methyl-1H-indole-2-carboxylic acid ethyl ester;SCHEMBL85706;MLS000038492;1H-Indole-2-carboxylic acid, 5-methyl-, ethyl ester;CHEMBL1518533;DTXSID50283326;5-methyl-2-(ethoxycarbonyl)indole;HMS2345F09;ethyl 5-methyl-2-indolecarboxylate;BBL012856;NSC-30928;STK158196;AKOS001476257;CS-W015452;PB41011;AC-26884;BP-12440;NS-00008;SMR000034076;SY040435;Ethyl 5-methylindole-2-carboxylate, 97%;EU-0000203;FT-0626132;EN300-317768;M-4084;O10710;SR-01000389771;5-Methyl-1H-indole-2-carboxylic acid, ethyl ester;SR-01000389771-1;Z293567284;5-Methylindole-2-carboxylic acid ethyl ester, NSC 30928

Chemical Property of Ethyl 5-methylindole-2-carboxylate

Chemical Property:

• Vapor Pressure: 2.9E-05mmHg at 25°C
• Melting Point: 162-164°C
• Refractive Index: 1.609
• Boiling Point: 356.5 °C at 760 mmHg
• PKA: 15.19±0.30(Predicted)
• Flash Point: 169.4 °C
• PSA: 42.09000
• Density: 1.177g/cm³
• LogP: 2.65300
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Soluble in methanol, and dichloromethane. Insoluble in water.
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 203.094628657
• Heavy Atom Count: 15
• Complexity: 242

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl 5-methylindole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=C(N1)C=CC(=C2)C
• Uses: Reactant for synthesis of oxazino[4,3-a]indoles via cascade addition-cyclization reactions 1 Reactant for preparation of indolecarboxamides as cannabinoid CB1 receptor antagonists 2 Reactant for preparation of indole-3-propionic acids as antiinflammatory and analgesic agents 3 Reactant for Friedel-Crafts acylation with nitrobenzoyl chloride 4 Reactant for oximation reactions 5 Reactant for synthesis of oxazino[4,3-a]indoles via cascade addition-cyclization reactions, reactant for preparation of indolecarboxamides as cannabinoid CB1 receptor antagonists, reactant for preparation of indole-3-propionic acids as antiinflammatory and analgesic agents, reactant for Friedel-Crafts acylation with nitrobenzoyl chloride. Indole ring system is an important building block or intermediate in the synthesis of many pharmaceutical agents. It is formed during the Fischer indolization of ethyl pyruvate 2-[2-(methanesulfonyloxy)-4-methyl]phenylhydrazine. ? Reactant for oximation reactions

Technology Process of Ethyl 5-methylindole-2-carboxylate

There total 23 articles about Ethyl 5-methylindole-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: 88.0%

3-(5-methyl-2-nitro-phenyl)-acrylic acid ethyl ester → 5-methyl-1H-indole-2-carboxylic acid ethyl ester (16382-15-3)

Guidance literature:

With triethyl phosphate; for 3h; Reflux;

DOI:10.5012/bkcs.2011.32.12.4309

Reference yield: 87.0%

(E)-ethyl 2-(p-tolylhydrazono)propanoate (91462-34-9) → 5-methyl-1H-indole-2-carboxylic acid ethyl ester (16382-15-3)

Guidance literature:

With amberlyst-15; In toluene; at 110 ℃; for 5h;

Reference yield: 78.0%

2-oxo-propionic acid ethyl ester (617-35-6) + p-toluidine (106-49-0,12221-03-3) → 5-methyl-1H-indole-2-carboxylic acid ethyl ester (16382-15-3)

Guidance literature:

With oxygen; palladium diacetate; acetic acid; In dimethyl sulfoxide; at 70 ℃; for 18h; under 760.051 Torr; Schlenk technique; Molecular sieve;

DOI:10.1021/acs.joc.8b02180

upstream raw materials:

ethanol

2-p-tolylhydrazono-propionic acid

(E)-ethyl 2-(p-tolylhydrazono)propanoate

2,4-dimethylnitrobenzene

Downstream raw materials:

5-methyl-indole-2-carboxylic acid benzylidenehydrazide

5-Methyl-2-(5-phenyl-[1,3,4]oxadiazol-2-yl)-1H-indole

5-Methyl-1H-indole-2-carboxylic acid [1-(4-methoxy-phenyl)-meth-(E)-ylidene]-hydrazide

2-[5-(4-Methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-5-methyl-1H-indole

Refernces

• 1、 Wang, Lei,Fang, Kun,Cheng, Junfei,Li, Yu,Huang, Yahui,Chen, Shuqiang,Dong, Guoqiang,Wu, Shanchao,Sheng, Chunquan. "Scaffold Hopping of Natural Product Evodiamine: Discovery of a Novel Antitumor Scaffold with Excellent Potency against Colon Cancer". . p. 696 - 713. Retrieved 2020/02/04.
• 2、 Ren, Long,Nan, Guanglei,Wang, Yongcheng,Xiao, Zhiyan. "Carboxylic Acid-Promoted Single-Step Indole Construction from Simple Anilines and Ketones via Aerobic Cross-Dehydrogenative Coupling". . p. 14472 - 14488. Retrieved 2018/11/23.