Methyl 3-amino-7-methoxybenzo[b]thiophene-2-carboxylate

Base Information

• Chemical Name: Methyl 3-amino-7-methoxybenzo[b]thiophene-2-carboxylate
• CAS No.: 198204-08-9
• Molecular Formula: C11H11NO3S
• Molecular Weight: 237.27
• Mol file: 198204-08-9.mol

Synonyms:Methyl 3-amino-7-methoxybenzo[b]thiophene-2-carboxylate

Chemical Property of Methyl 3-amino-7-methoxybenzo[b]thiophene-2-carboxylate

Chemical Property:

• Boiling Point: 399.6±37.0 °C(Predicted)
• PSA: 89.79000
• Density: 1.338±0.06 g/cm3(Predicted)
• LogP: 2.85990

Purity/Quality:

99% ^*data from raw suppliers

Methyl3-amino-7-methoxybenzo[b]thiophene-2-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl 3-amino-7-methoxybenzo[b]thiophene-2-carboxylate

There total 4 articles about Methyl 3-amino-7-methoxybenzo[b]thiophene-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: 94.0%

Methyl thioglycolate (2365-48-2) + 2-fluoro-3-methoxybenzonitrile (198203-94-0) → methyl 3-amino-7-methoxy-1-benzo[b]thiophene-2-carboxylate (198204-08-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 1.5h; Inert atmosphere;

Reference yield: 68.0%

3-methoxy-2-nitrobenzonitrile (142596-50-7) + Methyl thioglycolate (2365-48-2) → methyl 3-amino-7-methoxy-1-benzo[b]thiophene-2-carboxylate (198204-08-9)

Guidance literature:

With water; potassium hydroxide; In 1,2-dimethoxyethane; at -5 - 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jm400043d

Reference yield:

2-fluoro-3-methoxybenzoic acid (137654-20-7) → methyl 3-amino-7-methoxy-1-benzo[b]thiophene-2-carboxylate (198204-08-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) (COCl)2, DMF, 2.) NH₃ / 1.) CH₂Cl₂, 25 deg C, 3.5 h, 2.) CH₂Cl₂, 20 min

2: 53 percent / P₂O₅, hexamethyl disiloxane / various solvent(s) / 4 h / 100 °C

3: 1.) NaH / 1.) DMSO, 25 deg C, 2.) DMSO, 3 h

With oxalyl dichloride; Hexamethyldisiloxane; ammonia; phosphorus pentoxide; sodium hydride; N,N-dimethyl-formamide; In various solvent(s);

DOI:10.1002/jhet.5570340412

upstream raw materials:

Methyl thioglycolate

2-fluoro-3-methoxybenzonitrile

2-fluoro-3-methoxybenzoic acid

2-fluoro-3-methoxybenzamide

Downstream raw materials:

C₂₀H₂₁NO₆S

Refernces

• 1、 Romagnoli, Romeo,Baraldi, Pier Giovanni,Kimatrai Salvador, Maria,Preti, Delia,Aghazadeh Tabrizi, Mojgan,Bassetto, Marcella,Brancale, Andrea,Hamel, Ernest,Castagliuolo, Ignazio,Bortolozzi, Roberta,Basso, Giuseppe,Viola, Giampietro. "Synthesis and biological evaluation of 2-(alkoxycarbonyl)-3-anilinobenzo[b] thiophenes and thieno[2,3-b]pyridines as new potent anticancer agents". supporting information. p. 2606 - 2618. Retrieved 2013/05/09.