Methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate

Base Information

• Chemical Name: Methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate
• CAS No.: 111042-90-1
• Molecular Formula: C9H8N2O2S
• Molecular Weight: 208.241
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID20549608
• Nikkaji Number: J2.808.246K
• Wikidata: Q72487472
• Mol file: 111042-90-1.mol

Synonyms:Methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate;111042-90-1;3-AMINO-THIENO[3,2-B]PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER;SCHEMBL843791;DTXSID20549608;FFHLOZJKPAWEAX-UHFFFAOYSA-N;AMY21016;MFCD08448152;AKOS015852051;THIENO[3,2-B]PYRIDINE-2-CARBOXYLIC ACID, 3-AMINO-, METHYL ESTER;PB27925;SB10376;AS-30514;CS-0049125;EN300-122207;A802278;J-010697;W-204747

Chemical Property of Methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 122 °C
• Refractive Index: 1.7
• Boiling Point: 377.553 °C at 760 mmHg
• PKA: 4.05±0.40(Predicted)
• Flash Point: 182.138 °C
• PSA: 93.45000
• Density: 1.422 g/cm³
• LogP: 2.24630
• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 208.03064868
• Heavy Atom Count: 14
• Complexity: 237

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl3-Aminothieno[3,2-b]pyridine-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C2=C(S1)C=CC=N2)N

Technology Process of Methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate

There total 5 articles about Methyl 3-aminothieno[3,2-b]pyridine-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: 95.0%

Methyl thioglycolate (2365-48-2) + 3-fluoropicolinonitrile (97509-75-6) → methyl 3-amino-thieno[3,2-b]pyridine-2-carboxylate (111042-90-1)

Guidance literature:

With potassium hydroxide; In water; N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1016/j.tetlet.2009.10.138

Reference yield: 84.0%

3-chloro-2-cyanopyridine (38180-46-0) + Methyl thioglycolate (2365-48-2) → methyl 3-amino-thieno[3,2-b]pyridine-2-carboxylate (111042-90-1)

Guidance literature:

With potassium carbonate; In chloroform; water; N,N-dimethyl-formamide;

Reference yield:

3-chloropyridine-N-oxide (1851-22-5) → methyl 3-amino-thieno[3,2-b]pyridine-2-carboxylate (111042-90-1)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / acetonitrile / 20 h / Reflux

2: potassium carbonate / acetonitrile / 3 h / Reflux

With potassium carbonate; triethylamine; In acetonitrile;

upstream raw materials:

3-chloro-2-cyanopyridine

Methyl thioglycolate

3-fluoropicolinonitrile

3-chloropyridine-N-oxide

Downstream raw materials:

methyl thieno[3,2-b]pyridine-2-carboxylate

methyl 3-(2-nitrophenylamino)thieno[3,2-b]pyridine-2-carboxylate

methyl 3-(4-nitrophenylamino)thieno[3,2-b]pyridine-2-carboxylate

methyl 3-(4-aminophenylamino)thieno[3,2-b]pyridine-2-carboxylate

Refernces

• 1、 -. "SULFONAMIDES AS TRPM8 MODULATORS". Page/Page column 89. . Retrieved 2012/07/31.
• 2、 -. "CERTAIN TRIAZOLOPYRIDINES AND TRIAZOLOPYRAZINES, COMPOSITIONS THEREOF AND METHODS OF USE THEREFOR". Page/Page column 25. . Retrieved 2011/07/30.