methyl 4-ethenyl-1H-pyrrole-2-carboxylate

Base Information

• Chemical Name: methyl 4-ethenyl-1H-pyrrole-2-carboxylate
• CAS No.: 198703-17-2
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.165
• DSSTox Substance ID: DTXSID40596235
• Wikidata: Q82491443
• Mol file: 198703-17-2.mol

Synonyms:198703-17-2;methyl 4-ethenyl-1H-pyrrole-2-carboxylate;1H-Pyrrole-2-carboxylicacid,4-ethenyl-,methylester(9CI);Methyl 4-vinyl-1H-pyrrole-2-carboxylate;SCHEMBL7497472;DTXSID40596235;VCXXDJWJJSFYLL-UHFFFAOYSA-N

Chemical Property of methyl 4-ethenyl-1H-pyrrole-2-carboxylate

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 151.063328530
• Heavy Atom Count: 11
• Complexity: 168

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1=CC(=CN1)C=C

Technology Process of methyl 4-ethenyl-1H-pyrrole-2-carboxylate

There total 3 articles about methyl 4-ethenyl-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:

methyl 4-bromo-1H-pyrrole-2-carboxylate (934-05-4) + 2,4,6-trivinylcyclotriboroxane*pyridine complex → methyl 4-ethenyl-1H-pyrrole-2-carboxylate (198703-17-2)

Guidance literature:

With potassium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,1'-bis(di-tertbutylphosphino)ferrocene; In 1,4-dioxane; water; at 95 ℃; for 3h; Inert atmosphere;

Reference yield:

C14H13NO4S → methyl 4-ethenyl-1H-pyrrole-2-carboxylate (198703-17-2)

Guidance literature:

With sodium methylate; In methanol; at 50 ℃; for 12h; Concentration;

Reference yield:

methyl N-benzenesulfonyl-4-bromopyrrole-2-carboxylate (882747-46-8) → methyl 4-ethenyl-1H-pyrrole-2-carboxylate (198703-17-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 24 h / 100 °C / Inert atmosphere

1.2: 6 h

2.1: sodium methylate / methanol / 12 h / 50 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium methylate; In methanol; N,N-dimethyl-formamide;

upstream raw materials:

methyl 4-bromo-1H-pyrrole-2-carboxylate

methyl N-benzenesulfonyl-4-bromopyrrole-2-carboxylate

Downstream raw materials:

methyl 4-ethyl-pyrrole-2carboxylate

methyl 5-vinylpyrrole-3-carboxylate