methyl 3-formyl-1H-indole-2-carboxylate

Base Information

• Chemical Name: methyl 3-formyl-1H-indole-2-carboxylate
• CAS No.: 18450-26-5
• Molecular Formula: C11H9 N O3
• Molecular Weight: 203.197
• Hs Code.: 2933990090
• European Community (EC) Number: 851-179-4
• DSSTox Substance ID: DTXSID30352847
• Wikidata: Q82130237
• Mol file: 18450-26-5.mol

Synonyms:methyl 3-formyl-1H-indole-2-carboxylate;18450-26-5;methyl 3-formylindole-2-carboxylate;Methyl3-Formyl-1h-Indole-2-Carboxylate;3-formyl-1h-indole-2-carboxylic acid methyl ester;1h-indole-2-carboxylic acid,3-formyl-,methyl ester;MFCD03848053;SCHEMBL2800262;DTXSID30352847;1H-INDOLE-2-CARBOXYLIC ACID, 3-FORMYL-, METHYL ESTER;BBL030116;STL372885;AKOS004116843;SY033435;3-FORMYL-2-(METHOXYCARBONYL)INDOLE;A4086;CS-0105026;FT-0680164;EN300-183201;9W-0364;J-522172;Methyl 3-formyl-1H-indole-2-carboxylate, AldrichCPR;Z1509145440

Chemical Property of methyl 3-formyl-1H-indole-2-carboxylate

Chemical Property:

• Vapor Pressure: 2.23E-07mmHg at 25°C
• Melting Point: 206-208°C
• Boiling Point: 423.5°Cat760mmHg
• PKA: 13.48±0.30(Predicted)
• Flash Point: 209.9°C
• PSA: 59.16000
• Density: 1.341g/cm³
• LogP: 1.76700
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 203.058243149
• Heavy Atom Count: 15
• Complexity: 267

Purity/Quality:

98%min ^*data from raw suppliers

Methyl3-Formyl-1H-indole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1=C(C2=CC=CC=C2N1)C=O

Technology Process of methyl 3-formyl-1H-indole-2-carboxylate

There total 4 articles about methyl 3-formyl-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: 90.0%

indole-2-carboxylic acid methyl ester (1202-04-6) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → methyl 3-formyl-1H-indole-2-carboxylate (18450-26-5)

Guidance literature:

With trichlorophosphate; at 20 - 60 ℃; for 4.5h;

DOI:10.1021/jo0514974

Reference yield:

indole-2-carboxylic acid methyl ester (1202-04-6) + formyl chloride (2565-30-2) → methyl 3-formyl-1H-indole-2-carboxylate (18450-26-5)

Guidance literature:

With aluminum (III) chloride; In 1,2-dichloro-ethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1002/chem.201900425

Reference yield:

Indole-2-carboxylic acid (1477-50-5,1228050-17-6) → methyl 3-formyl-1H-indole-2-carboxylate (18450-26-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sulfuric acid / 24 h / Reflux; Inert atmosphere

2.1: trichlorophosphate / 0.17 h / 0 °C / Inert atmosphere

2.2: 4.67 h / 0 - 60 °C / Inert atmosphere

2.3: pH 8 / Cooling; Inert atmosphere

With sulfuric acid; trichlorophosphate; 2.1: |Vilsmeier-Haack Formylation / 2.2: |Vilsmeier-Haack Formylation / 2.3: |Vilsmeier-Haack Formylation;

DOI:10.1080/14756366.2018.1493473

upstream raw materials:

indole-2-carboxylic acid methyl ester

N,N-dimethyl-formamide

Indole-2-carboxylic acid

formyl chloride

Downstream raw materials:

methyl 3-formyl-1-ethyl-1H-indole-2-carboxylate

methyl 3-formyl-1-benzyl-1H-indole-2-carboxylate

3-formyl-indole-2-carboxylic acid

methyl 3-formyl-1-methyl-1H-indole-2-carboxylate

Refernces

• 1、 Kryshchyshyn-Dylevych, Anna,Garazd, Myroslav,Karkhut, Andrew,Polovkovych, Sviatoslav,Lesyk, Roman. "Synthesis and anticancer activity evaluation of 3-(4-oxo-2-thioxothiazolidin-5-yl)-1H-indole-carboxylic acids derivatives". supporting information. p. 2830 - 2838. Retrieved 2020/07/14.
• 2、 Preti, Delia,Romagnoli, Romeo,Rondanin, Riccardo,Cacciari, Barbara,Hamel, Ernest,Balzarini, Jan,Liekens, Sandra,Schols, Dominique,Estévez-Sarmiento, Francisco,Quintana, José,Estévez, Francisco. "Design, synthesis, in vitro antiproliferative activity and apoptosis-inducing studies of 1-(3′,4′,5′-trimethoxyphenyl)-3-(2′-alkoxycarbonylindolyl)-2-propen-1-one derivatives obtained by a molecular hybridisation approach". . p. 1225 - 1238. Retrieved 2018/09/04.