Ethyl 5-cyanoindole-2-carboxylate

Base Information

• Chemical Name: Ethyl 5-cyanoindole-2-carboxylate
• CAS No.: 105191-13-7
• Molecular Formula: C12H10N2O2
• Molecular Weight: 214.224
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID80405796
• Nikkaji Number: J3.026.334K
• Wikidata: Q72473925
• Mol file: 105191-13-7.mol

Synonyms:Ethyl 5-cyanoindole-2-carboxylate;105191-13-7;ethyl 5-cyano-1H-indole-2-carboxylate;5-CYANOINDOLE-2-CARBOXYLIC ACID ETHYL ESTER;1H-Indole-2-carboxylic acid, 5-cyano-, ethyl ester;5-Cyano-1H-indole-2-carboxylic acid ethyl ester;MFCD04966999;Oprea1_392951;SCHEMBL1420412;DTXSID80405796;VZSOXWAHGVEQOT-UHFFFAOYSA-N;BBL020536;STK893225;AKOS001476078;AC-5211;CS-W022704;FS-3361;NCGC00335620-01;SY019812;AM20020148;FT-0689438;C-8890;5-Cyano-1H-indole-2carboxylic acid ethyl ester;AB01328156-02;A801160;methyl 5-cyano-1H-indole-2-carboxylate;Ethyl 5-Cyanoindole-2-carboxylate

Chemical Property of Ethyl 5-cyanoindole-2-carboxylate

Chemical Property:

• Vapor Pressure: 3.06E-07mmHg at 25°C
• Refractive Index: 1.622
• Boiling Point: 419.334 °C at 760 mmHg
• PKA: 13.63±0.30(Predicted)
• Flash Point: 207.406 °C
• PSA: 65.88000
• Density: 1.29 g/cm³
• LogP: 2.21628
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 214.074227566
• Heavy Atom Count: 16
• Complexity: 320

Purity/Quality:

97% ^*data from raw suppliers

Ethyl5-Cyanoindole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=C(N1)C=CC(=C2)C#N

Technology Process of Ethyl 5-cyanoindole-2-carboxylate

There total 10 articles about Ethyl 5-cyanoindole-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: 63.0%

ethyl 5-bromoindolecarboxylate (16732-70-0) + copper(I) cyanide (544-92-3) → 5-Cyano-1H-indole-2-carboxylic acid ethyl ester (105191-13-7)

Guidance literature:

In DMF (N,N-dimethyl-formamide); at 155 ℃; for 7h;

Reference yield: 54.0%

5-chloro-indole-2-carboxylic acid ethyl ester (4792-67-0) + urea (57-13-6) → 5-Cyano-1H-indole-2-carboxylic acid ethyl ester (105191-13-7)

Guidance literature:

With nickel(II) acetylacetonate; potassium fluoride; phenylsilane; zinc; bis(2-diphenylphosphinoethyl)phenylphosphine; In 1-methyl-pyrrolidin-2-one; at 120 ℃; for 20h;

DOI:10.1038/s41467-020-17939-2

Reference yield: 50.0%

ethyl 2-ethoxyacrylate (22121-86-4) + 4-amino-3-iodobenzonitrile (33348-34-4) → 5-Cyano-1H-indole-2-carboxylic acid ethyl ester (105191-13-7) + C12H10N2O2

Guidance literature:

With tetrabutylammomium bromide; palladium diacetate; sodium hydrogencarbonate; In acetonitrile; at 80 ℃; for 96h; Inert atmosphere;

DOI:10.1002/ejoc.201101072

upstream raw materials:

(5-cyano-2-nitro-phenyl)-pyruvic acid ethyl ester

3-methyl-4-nitrobenzonitrile

ethyl 5-bromoindolecarboxylate

copper(I) cyanide

Downstream raw materials:

5-cyano-1H-indole-2-carboxylic acid

4-{4-[(5-carbamimidoyl-1-methyl-1H-indol-2-ylmethyl)-methanesulfonyl-amino]-phenoxy}-piperidine-1-carboxylic acid tert-butyl ester

5-cyano-1H-indole-2-carboxylic acid methyl ester

ethyl 5-cyano-1-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-indole-2-carboxylate