methyl 4H-thieno[3,2-b]pyrrole-2-carboxylate

Base Information

• Chemical Name: methyl 4H-thieno[3,2-b]pyrrole-2-carboxylate
• CAS No.: 749261-96-9
• Molecular Formula: C8H7NO2S
• Molecular Weight: 181.215
• European Community (EC) Number: 859-991-0
• Mol file: 749261-96-9.mol

Synonyms:methyl 4H-thieno[3,2-b]pyrrole-2-carboxylate;749261-96-9;SCHEMBL1245204;OSZRKQNJIOWIFE-UHFFFAOYSA-N;AT36396;methyl4H-thieno[3,2-b]pyrrole-2-carboxylate;EN300-191350;Z335829208

Chemical Property of methyl 4H-thieno[3,2-b]pyrrole-2-carboxylate

Chemical Property:

• PSA: 70.33000
• LogP: 2.01600
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 181.01974964
• Heavy Atom Count: 12
• Complexity: 198

Purity/Quality:

4H-Thieno[3,2-b]pyrrole-2-carboxylicacidmethylester 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC2=C(S1)C=CN2

Technology Process of methyl 4H-thieno[3,2-b]pyrrole-2-carboxylate

There total 5 articles about methyl 4H-thieno[3,2-b]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: 87.0%

methyl 5-[(E)-2-(dimethylamino)ethenyl]-4-nitrothiophene-2-carboxylate (749261-94-7) → 4H-thieno[3,2-b]pyrrole-2-carboxylic acid methyl ester (749261-96-9)

Guidance literature:

With hydrogen; 5%-palladium/activated carbon; In tetrahydrofuran; acetic acid; at 20 ℃; for 16h; under 2660.18 Torr;

Reference yield:

methyl 5-[2-(dimethylamino)ethenyl]-4-nitrothiophene-2-carboxylate (1007389-09-4) → 4H-thieno[3,2-b]pyrrole-2-carboxylic acid methyl ester (749261-96-9)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; acetic acid; In tetrahydrofuran; for 48h; under 2585.81 Torr;

Reference yield:

5-methyl-4-nitro-thiophene-2-carboxylic acid (36050-35-8) → 4H-thieno[3,2-b]pyrrole-2-carboxylic acid methyl ester (749261-96-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / HCO₂NH₄ / Pd/C / methanol

With ammonium formate; palladium on activated charcoal; In methanol;

DOI:10.1070/MC2004v014n01ABEH001877

upstream raw materials:

methyl 5-[(E)-2-(dimethylamino)ethenyl]-4-nitrothiophene-2-carboxylate

5-methyl-4-nitro-thiophene-2-carboxylic acid

methyl 5-[2-(dimethylamino)ethenyl]-4-nitrothiophene-2-carboxylate

5-methyl-4-nitro-thiophene-2-carboxylic acid methyl ester

Downstream raw materials:

4H-thieno[3,2-b]pyrrole-2-carboxylic acid

methyl 6-cyclohex-1-en-1-yl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Refernces

• 1、 -. "BICYCLIC HETEROCYCLIC COMPOUNDS AS ROR GAMMA MODULATORS". Page/Page column 34. . Retrieved 2015/02/02.
• 2、 -. "FLUORO-SUBSTITUTED INHIBITORS OF D-AMINO ACID OXIDASE". Page/Page column 83. . Retrieved 2008/06/13.