5556-20-7

Basic information

• Product Name: ethyl 3-hydroxybenzo[b]thiophene-2-carboxylate
• Synonyms: ethyl 3-hydroxybenzo[b]thiophene-2-carboxylate
• CAS NO: 5556-20-7
• Molecular Formula: C₁₁H₁₀O₃S
• Molecular Weight: 222.2603
• Mol File: 5556-20-7.mol
• Article Data: 8

Chemical Properties

• Melting Point: 73-74 °C
• Boiling Point: 344.4±22.0 °C(Predicted)
• Appearance: /
• Density: 1.340±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 7.47±0.50(Predicted)
• CAS DataBase Reference: ethyl 3-hydroxybenzo[b]thiophene-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-hydroxybenzo[b]thiophene-2-carboxylate(5556-20-7)
• EPA Substance Registry System: ethyl 3-hydroxybenzo[b]thiophene-2-carboxylate(5556-20-7)

Safety Data

• Hazardous Substances Data: 5556-20-7(Hazardous Substances Data)

Usage

General Description

Ethyl 3-hydroxybenzo[b]thiophene-2-carboxylate is a chemical compound with the molecular formula C13H12O4S and a molar mass of 260.3 g/mol. It is commonly used as an intermediate in the synthesis of pharmaceuticals and organic compounds, and it also has potential applications in the field of organic chemistry and material science. The compound is a white to beige solid with a characteristic odor, and it is soluble in organic solvents such as ethanol, methanol, and dichloromethane. Ethyl 3-hydroxybenzo[b]thiophene-2-carboxylate is known for its unique structure and properties, making it a valuable chemical in various research and industrial applications.

Upstream product

• 1190582-62-7 2-benzoyl-2-ethoxycarbonylbenzo[b]thiophen-3(2H)-one 
• 3950-02-5 2-chlorosulfenylbenzoyl chloride 
• 141-97-9 ethyl acetoacetate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 105-53-3 diethyl malonate 
• 4892-02-8 Methyl thiosalicylate 
• 105-36-2 ethyl bromoacetate 
• 19602-82-5 2,2'-dithiodibenzoic acid dichloride 
• 120571-33-7 ethyl 3-(2-benzylsulphinyl)phenyl-2-diazo-3-oxopropanoate 
• 131327-52-1 ethyl 2-diazo-3-hydroxy-3-(2-phenylthio)phenylpropanoate 
• 131327-55-4 ethyl 3-(2-benzylthio)phenyl-2-diazo-3-oxopropanoate 
• 36943-39-2 2-(phenylthio)benzaldehyde 
• 120571-35-9 ethyl 1-benzyl-2,3-dihydro-3-oxobenzothiophene-1-oxide-2-carboxylate, inner salt 
• 52140-90-6 4-hydroxy-3-nitro-1-thioumarin 

Downstream Products

• 1416051-61-0 tert-butyl 4-((2-(ethoxycarbonyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate 
• 1416051-64-3 tert-butyl 4-((2-((benzyloxy)carbonyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate 
• 1416051-67-6 benzyl 3-(piperidin-4-yloxy)benzo[b]thiophene-2-carboxylate 
• 1416051-66-5 tert-butyl 4-((2-(((3-methoxybenzyl)oxy)carbonyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate 
• 19354-50-8 3-methoxy-1-benzothiophene-2-carboxylic acid 
• 19354-51-9 methyl 3-methoxybenzothiophene-2-carboxylate 
• 722517-00-2 3-benzyloxy-5-methoxy-1-benzo[b]thiophene-2-carboxylic acid 

Relevant articles and documents

Accepting the Invitation to Open Innovation in Malaria Drug Discovery: Synthesis, Biological Evaluation, and Investigation on the Structure-Activity Relationships of Benzo[b]thiophene-2-carboxamides as Antimalarial Agents

Malaria eradication is a global health priority, but current therapies are not always suitable for providing a radical cure. Artemisinin has paved the way for the current malaria treatment, the so-called Artemisinin-based Combination Therapy (ACT). However, with the detection of resistance to ACT, innovative compounds active against multiple parasite species and at multiple life stages are needed. GlaxoSmithKline has recently disclosed the results of a phenotypic screening of an internal library, publishing a collection of 400 antimalarial chemotypes, termed the “Malaria Box”. After analysis of the data set, we have carried out a medicinal chemistry campaign in order to define the structure-activity relationships for one of the released compounds, which embodies a benzothiophene-2-carboxamide core. Thirty-five compounds were prepared, and a description of the structural features responsible for the in vitro activity against different strains of P. falciparum, the toxicity, and the metabolic stability is herein reported.

Discovery of novel and ligand-efficient inhibitors of plasmodium falciparum and plasmodium vivax N-myristoyltransferase

N-Myristoyltransferase (NMT) is an attractive antiprotozoan drug target. A lead-hopping approach was utilized in the design and synthesis of novel benzo[b]thiophene-containing inhibitors of Plasmodium falciparum (Pf) and Plasmodium vivax (Pv) NMT. These inhibitors are selective against Homo sapiens NMT1 (HsNMT), have excellent ligand efficiency (LE), and display antiparasitic activity in vitro. The binding mode of this series was determined by crystallography and shows a novel binding mode for the benzothiophene ring.

A simple route to benzo[b]thiophenes: Sulfanylation-acylation of C-H acids with 2-(chlorosulfanyl)benzoyl chloride

A convenient procedure for the preparation of 2,2-disubstituted benzo[b]thiophen3(2H)-ones and 2-substituted 3-hydroxybenzo[b]thiophenes from β-diketones, β-keto- and β-cyanoesters, and β-cyanoketones, diethyl malonate, malonitrile, and anthrone has been