Ethyl 4-cyano-1H-pyrrole-2-carboxylate

Base Information

• Chemical Name: Ethyl 4-cyano-1H-pyrrole-2-carboxylate
• CAS No.: 944901-09-1
• Molecular Formula: C₈H₈N₂O₂
• Molecular Weight: 164.164
• Hs Code.: 2933990090
• European Community (EC) Number: 870-405-2
• DSSTox Substance ID: DTXSID00695137
• Nikkaji Number: J3.261.994K
• Wikidata: Q82624193
• Mol file: 944901-09-1.mol

Synonyms:944901-09-1;ETHYL 4-CYANO-1H-PYRROLE-2-CARBOXYLATE;ETHYL 4-CYANOPYRROLE-2-CARBOXYLATE;4-Cyano-1H-pyrrole-2-carboxylic acid ethyl ester;Ethyl4-cyano-1H-pyrrole-2-carboxylate;SCHEMBL21929421;DTXSID00695137;MFCD10696319;AKOS006302917;AB57039;AS-37762;CS-0172310;A916566

Chemical Property of Ethyl 4-cyano-1H-pyrrole-2-carboxylate

Chemical Property:

• PSA: 65.88000
• LogP: 1.06308
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 164.058577502
• Heavy Atom Count: 12
• Complexity: 218

Purity/Quality:

97% ^*data from raw suppliers

Ethyl4-cyano-1H-pyrrole-2-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC(=CN1)C#N

Technology Process of Ethyl 4-cyano-1H-pyrrole-2-carboxylate

There total 2 articles about Ethyl 4-cyano-1H-pyrrole-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: 93.0%

potassiumhexacyanoferrate(II) trihydrate + 4-bromo-1H-pyrrole-2-carboxylic acid ethyl ester (433267-55-1) → ethyl 4-cyano-1H-pyrrole-2-carboxylate (944901-09-1)

Guidance literature:

With C₄₂H₅₈NO₃PPdS^(2-); potassium acetate; tert-butyl XPhos; In 1,4-dioxane; water; at 100 ℃; for 1h; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.201304188

Reference yield:

isocyanate de chlorosulfonyle (1189-71-5) + ethyl 1H-pyrrole-2-carboxylate (2199-43-1) → ethyl 4-cyano-1H-pyrrole-2-carboxylate (944901-09-1) + 5-cyano-1H-pyrrole-2-carboxylic acid methyl ester (937-19-9)

Guidance literature:

In N,N-dimethyl-formamide; acetonitrile; Overall yield = 35 %;

DOI:10.1016/j.bmcl.2014.04.061

Reference yield:

ethyl 4-cyano-1H-pyrrole-2-carboxylate (944901-09-1) → C16H17BrN2O3 (1610627-22-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / N,N-dimethyl-formamide

2: hydrogen; ammonium hydroxide

3: N-ethyl-N,N-diisopropylamine / acetonitrile

With ammonium hydroxide; hydrogen; sodium hydride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmcl.2014.04.061

upstream raw materials:

4-bromo-1H-pyrrole-2-carboxylic acid ethyl ester

isocyanate de chlorosulfonyle

ethyl 1H-pyrrole-2-carboxylate

Downstream raw materials:

C₁₆H₁₇BrN₂O₃

ethoxymethyl

C₂₅H₂₂FN₃O₂