6H-thieno[2,3-b]pyrrole-5-carboxylic acid

Base Information

• Chemical Name: 6H-thieno[2,3-b]pyrrole-5-carboxylic acid
• CAS No.: 51856-25-8
• Molecular Formula: C7H5NO2S
• Molecular Weight: 167.19
• Hs Code.: 2934999090
• European Community (EC) Number: 853-572-6
• ChEMBL ID: CHEMBL496305
• DSSTox Substance ID: DTXSID30469565
• Pharos Ligand ID: DALR1HNDM2B9
• Wikidata: Q27455330
• Mol file: 51856-25-8.mol

Synonyms:6H-thieno[2,3-b]pyrrole-5-carboxylic acid;51856-25-8;DAO-IN-1;CHEMBL496305;SCHEMBL1244615;DTXSID30469565;SEPXFZLYPWFMSY-UHFFFAOYSA-N;AMY10731;BCA85625;thieno[2,3-b]pyrrole-5-carboxylic;BDBM50260727;MFCD02664526;AKOS015901405;HY-W037417;AS-65106;CS-0093690;FT-0764265;EN300-26873;C90264;Q27455330;F8889-5032;Z235000792;4ZA

Chemical Property of 6H-thieno[2,3-b]pyrrole-5-carboxylic acid

Chemical Property:

• Melting Point: 207 °C (decomp)
• Boiling Point: 437.4 °C at 760 mmHg
• PKA: 4.37±0.30(Predicted)
• Flash Point: 218.3 °C
• PSA: 81.33000
• Density: 1.609 g/cm³
• LogP: 1.92760
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 167.00409958
• Heavy Atom Count: 11
• Complexity: 185

Purity/Quality:

NLT 98% ^*data from raw suppliers

6H-thieno[2,3-b]pyrrole-5-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC2=C1C=C(N2)C(=O)O

Technology Process of 6H-thieno[2,3-b]pyrrole-5-carboxylic acid

There total 7 articles about 6H-thieno[2,3-b]pyrrole-5-carboxylic acid 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: 97.7%

ethyl thieno<2,3-b>pyrrole-5-carboxylate (35357-56-3) → 6H-thieno[2,3-b]pyrrole-5-carboxylic acid (51856-25-8)

Guidance literature:

ethyl thieno<2,3-b>pyrrole-5-carboxylate; With sodium hydroxide; ethanol; water; for 1h; Heating / reflux;

With hydrogenchloride; water; In ethanol; at 20 ℃; for 0.5h;

Reference yield: 7.5%

→ 6H-thieno[2,3-b]pyrrole-5-carboxylic acid (51856-25-8)

Guidance literature:

Reference yield:

3-thiophene carboxaldehyde (498-62-4) → 6H-thieno[2,3-b]pyrrole-5-carboxylic acid (51856-25-8)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOEt / ethanol / 2 h / 0 - 20 °C

2: 1.2 g / xylene / 145 °C

3: aq. LiOH / tetrahydrofuran; methanol / 65 °C

With lithium hydroxide; sodium ethanolate; In tetrahydrofuran; methanol; ethanol; xylene; 2: Hemetsberger reaction;

DOI:10.1021/jm0502081

upstream raw materials:

ethyl thieno<2,3-b>pyrrole-5-carboxylate

methyl 6H-thieno[2,3-b]pyrrole-5-carboxylate

N-(3-formyl-thiophen-2-yl)-acetamide

3-thiophene carboxaldehyde

Downstream raw materials:

6H-thieno[2,3-b]pyrrole

Refernces

• 1、 Sparey, Tim,Abeywickrema, Pravien,Almond, Sarah,Brandon, Nick,Byrne, Noel,Campbell, Alister,Hutson, Pete H.,Jacobson, Marlene,Jones, Brian,Munshi, Sanjeev,Pascarella, Danette,Pike, Andrew,Prasad, G. Sridhar,Sachs, Nancy,Sakatis, Melanie,Sardana, Vinod,Venkatraman, Shankar,Young, Mary Beth. "The discovery of fused pyrrole carboxylic acids as novel, potent d-amino acid oxidase (DAO) inhibitors". scheme or table. p. 3386 - 3391. Retrieved 2009/04/06.
• 2、 -. "USE OF FUSED PYRROLE CARBOXYLIC ACIDS FOR THE TREATMENT OF NEURODEGENERATIVE AND PSYCHIATRIC DISEASES AS D-AMINO ACID OXIDASE INHIBITORS". Page/Page column 17. . Retrieved 2008/06/13.