Methyl 5-cyano-1H-pyrrole-2-carboxylate

Base Information

• Chemical Name: Methyl 5-cyano-1H-pyrrole-2-carboxylate
• CAS No.: 937-19-9
• Molecular Formula: C7H6 N2 O2
• Molecular Weight: 150.13
• Hs Code.: 2933990090
• European Community (EC) Number: 836-485-8
• DSSTox Substance ID: DTXSID50508324
• Wikidata: Q82365145
• Mol file: 937-19-9.mol

Synonyms:Methyl 5-cyano-1H-pyrrole-2-carboxylate;937-19-9;SCHEMBL3285053;DTXSID50508324;OOGGAVZXGHAZIG-UHFFFAOYSA-N;MFCD12924294;AKOS022175914;SB62108;Methyl5-cyano-1H-pyrrole-2-carboxylate;DS-11696;CS-0150820;C77228;EN300-244082;A917098;1H-Pyrrole-2-carboxylic acid, 5-cyano-, methyl ester;1H-Pyrrole-2-carboxylicacid,5-cyano-,methylester(9ci);Z1255366169

Chemical Property of Methyl 5-cyano-1H-pyrrole-2-carboxylate

Chemical Property:

• PSA: 65.88000
• LogP: 0.67298
• Storage Temp.: 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 150.042927438
• Heavy Atom Count: 11
• Complexity: 206

Purity/Quality:

97% ^*data from raw suppliers

methyl5-cyano-1H-pyrrole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC=C(N1)C#N

Technology Process of Methyl 5-cyano-1H-pyrrole-2-carboxylate

There total 10 articles about Methyl 5-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: 71.0%

methyl 5-formyl-1H-pyrrole-2-carboxylate (1197-13-3) → 5-cyano-1H-pyrrole-2-carboxylic acid methyl ester (937-19-9)

Guidance literature:

methyl 5-formyl-1H-pyrrole-2-carboxylate; With AMINOHIPPURATE SODIUM; hydroxylamine hydrochloride; In methanol; for 1h; Reflux;

With trichlorophosphate; In N,N-dimethyl-formamide; at -20 - 20 ℃; for 2.5h;

DOI:10.1016/j.tet.2015.03.012

Reference yield: 24.0%

methyl Pyrrole-2-carboxylate (1193-62-0) + isocyanate de chlorosulfonyle (1189-71-5) → 5-cyano-1H-pyrrole-2-carboxylic acid methyl ester (937-19-9)

Guidance literature:

In N,N-dimethyl-formamide; acetonitrile; at -40 - 20 ℃; for 24h;

DOI:10.1021/jo400372c

Reference yield:

methyl Pyrrole-2-carboxylate (1193-62-0) + isocyanate de chlorosulfonyle (1189-71-5) → methyl 4-cyanopyrrole-2-carboxylate (937-18-8) + 5-cyano-1H-pyrrole-2-carboxylic acid methyl ester (937-19-9)

Guidance literature:

With N,N-dimethyl-formamide; Yield given. Multistep reaction; 1.) acetonitrile, ice bath, 5 min, room temp., overnight; 2.) ice bath then 50 deg C, 15 min;

upstream raw materials:

methyl Pyrrole-2-carboxylate

isocyanate de chlorosulfonyle

methyl 5-cyano-1-hydroxy-1H-pyrrole-2-carboxylate

ethyl 1H-pyrrole-2-carboxylate

Downstream raw materials:

C₁₃H₁₂N₆O

5-carboxy-1H-pyrrole-2-carbonitrile