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

Base Information

• Chemical Name: ethyl 3-formyl-1H-indole-2-carboxylate
• CAS No.: 18450-27-6
• Molecular Formula: C12H11NO3
• Molecular Weight: 217.224
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50408416
• Nikkaji Number: J284.206H
• Wikidata: Q82213891
• Mol file: 18450-27-6.mol

Synonyms:ethyl 3-formyl-1H-indole-2-carboxylate;18450-27-6;3-Formyl-1H-indole-2-carboxylic acid ethyl ester;MFCD01463252;ethyl 3-formylindole-2-carboxylate;Oprea1_266872;SCHEMBL3198815;2-ethoxycarbonyl-3-formylindole;AMY1897;DTXSID50408416;UHTMDXSOGQARCU-UHFFFAOYSA-N;AKOS001476060;AB-0014;ethyl3-formyl-1H-indole-2-carboxylate;SY226651;BB 0220516;CS-0105023;FT-0680766;EN300-28225;1H-Indole-2-carboxylicacid,3-formyl-,ethyl ester;A880770;AE-473/30088022;SR-01000143881;J-520876;SR-01000143881-1;Z248489102

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

Chemical Property:

• Vapor Pressure: 1.51E-07mmHg at 25°C
• Melting Point: 186-188 ºC
• Refractive Index: 1.655
• Boiling Point: 428.5 °C at 760 mmHg
• Flash Point: 212.9 °C
• PSA: 59.16000
• Density: 1.293 g/cm³
• LogP: 2.15710
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 217.07389321
• Heavy Atom Count: 16
• Complexity: 279

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl3-Formyl-1H-indole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

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

There total 11 articles about ethyl 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: 100.0%

2-carbethoxyindole (3770-50-1,117770-52-2) + N-methyl-N-phenylformamide (93-61-8) → ethyl 3-formyl-1H-indole-2-carboxylate (18450-27-6)

Guidance literature:

With trichlorophosphate; In 1,2-dichloro-ethane; for 1.5h; Heating / reflux;

Reference yield: 95.0%

2-carbethoxyindole (3770-50-1,117770-52-2) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → ethyl 3-formyl-1H-indole-2-carboxylate (18450-27-6)

Guidance literature:

N,N-dimethyl-formamide; With trichlorophosphate; at 0 ℃; for 0.166667h;

2-carbethoxyindole; at 0 - 60 ℃; for 3.5h;

DOI:10.1016/j.tetlet.2018.08.049

Reference yield: 95.0%

2-carbethoxyindole (3770-50-1,117770-52-2) → ethyl 3-formyl-1H-indole-2-carboxylate (18450-27-6)

Guidance literature:

With trichlorophosphate; In water; N,N-dimethyl-formamide;

upstream raw materials:

2-carbethoxyindole

hydrogen cyanide

N-methyl-N-phenylformamide

ethyl 3-((dimethylamino)-methyl)-1H-indole-2-carboxylate

Downstream raw materials:

Ethyl 3-(4-phenylpiperazin-1-ylmethyl)-1H-indole-2-carboxylate

ethyl 3-hydroxymethyl-indole-2-carboxylate

ethyl 3-formyl-1-(3-methoxybenzyl)-1H-indole-2-carboxylate

ethyl 3-formyl-N-(3,4-dichlorobenzyl)indole-2-carboxylate

Refernces

• 1、 Tan, Wei,Li, Xin,Gong, Yu-Xin,Ge, Meng-Di,Shi, Feng. "Highly diastereo- and enantioselective construction of a spiro[cyclopenta[b]indole-1,3′-oxindole] scaffold via catalytic asymmetric formal [3+2] cycloadditions". . p. 15901 - 15904. Retrieved 2014.
• 2、 Devi, Manju,Jadhav, Amol P.,Singh, Ravi P.. "KOH-mediated stereoselective alkylation of 3-bromooxindoles for the synthesis of 3,3′-disubstituted oxindoles with two contiguous all carbon quaternary centres". supporting information. p. 8445 - 8448. Retrieved 2021/05/25.
• 3、 Chizhova, Maria,Khoroshilova, Olesya,Dar'in, Dmitry,Krasavin, Mikhail. "Acetic anhydride to the rescue: Facile access to privileged 1,2,3,4-tetrahydropyrazino[1,2-a]indole core via the Castagnoli-Cushman reaction". supporting information. p. 3612 - 3615. Retrieved 2018/09/11.