92539-88-3

Basic information

• Product Name: Methyl 2-aminobenzo[b]thiophene-3-carboxylate
• Synonyms: Methyl 2-aminobenzo[b]thiophene-3-carboxylate;Methyl 2-aminobenzothiophene-3-carboxylate;3-amino-benzo[B]thiophene3-carboxylic acid methyl ester
• CAS NO: 92539-88-3
• Molecular Formula: C10H9NO2S
• Molecular Weight: 207.24896
• Mol File: 92539-88-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl 2-aminobenzo[b]thiophene-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-aminobenzo[b]thiophene-3-carboxylate(92539-88-3)
• EPA Substance Registry System: Methyl 2-aminobenzo[b]thiophene-3-carboxylate(92539-88-3)

Safety Data

• Hazardous Substances Data: 92539-88-3(Hazardous Substances Data)

Usage

Description

Methyl 2-aminobenzo[b]thiophene-3-carboxylate is a yellow solid organic chemical belonging to the benzo[b]thiophene class. It has a molecular formula of C12H9NO2S and a molecular weight of 235.27 g/mol, with a melting point of 115-116 °C.

Uses

Used in Pharmaceutical Industry:
Methyl 2-aminobenzo[b]thiophene-3-carboxylate is used as a versatile building block in the synthesis and production of pharmaceuticals. It serves as a starting material in the preparation of various biologically active compounds, contributing to the development of new drugs.
Used in Agrochemical Industry:
Methyl 2-aminobenzo[b]thiophene-3-carboxylate is also utilized in the synthesis and production of agrochemicals. Its role as a starting material in organic synthesis aids in the creation of compounds that can be used in agricultural applications, such as pesticides or herbicides, to improve crop protection and yield.

Upstream product

• 7311-77-5 2-acetylamino-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 4506-71-2 ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 108-94-1 cyclohexanone 
• 108354-78-5 methyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 88734-89-8 3-Hydroxy-2-nitro-4H-1-benzothiopyran-4-on 
• 92539-85-0 2-Nitrobenzothiophen-3-carbonsaeuremethylester 

Downstream Products

• 76872-40-7 2,4-dichloro-benzothieno<2,3-d>pyrimidine 

Relevant articles and documents

2-Aminobenzo[b]thiophenecarboxylic esters from 3-hydroxy-2-nitro-1-thiochromone

3-Hydroxy-2-nitro-1-thiochromone (1b), when mixed with basis in alcoholic solution, yields the 2-nitro-benzothiophene-3-carboxylates 4a and 4b as well as the 2-amino-3-benzothiophene-3-carboxylates 11a and 11b. Under the same conditions, 3-methoxy-2-nitro-1-thiochromone (1c) yields 3-amino-2-nitro-1-thiochromone (12). Compound 1b reacts with morpholine in dioxane to give 2-nitro-benzothiophene-3-carboxamide (10).

Development of thieno- and benzopyrimidinone inhibitors of the Hedgehog signaling pathway reveals PDE4-dependent and PDE4-independent mechanisms of action

From a high content in vivo screen for modulators of developmental patterning in embryonic zebrafish, we previously identified eggmanone (EGM1, 3) as a Hedgehog (Hh) signaling inhibitor functioning downstream of Smoothened. Phenotypic optimization studies for in vitro probe development utilizing a Gli transcription-linked stable luciferase reporter cell line identified EGM1 analogs with improved potency and aqueous solubility. Mechanistic profiling of optimized analogs indicated two distinct scaffold clusters: PDE4 inhibitors able to inhibit downstream of Sufu, and PDE4-independent Hh inhibitors functioning between Smo and Sufu. Each class represents valuable in vitro probes for elucidating the complex mechanisms of Hh regulation.

A simple synthesis of alkyl 2-aminobenzo[ b ]thiophene-3-carboxylates via an unexpected dehydrogenation of alkyl 2-amino-4,5,6,7-tetrahydrobenzo[ b ]thiophene-3-carboxylates

A simple method for the preparation of alkyl 2-aminobenzo[b]thiophene-3-carboxylates is described. Alkyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylates, generated from the Gewald three-component reaction between cyclohexanones, alkyl cyanoacet