243-68-5

Basic information

• Product Name: [1]benzothieno[3,2-b]quinoline
• Synonyms: [1]benzothieno[3,2-b]quinoline
• CAS NO: 243-68-5
• Molecular Formula: C₁₅H₉NS
• Molecular Weight: 235.30366
• Mol File: 243-68-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [1]benzothieno[3,2-b]quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: [1]benzothieno[3,2-b]quinoline(243-68-5)
• EPA Substance Registry System: [1]benzothieno[3,2-b]quinoline(243-68-5)

Safety Data

• Hazardous Substances Data: 243-68-5(Hazardous Substances Data)

Usage

General Description

Benzothieno[3,2-b]quinoline is a chemical compound with a fused tricyclic ring structure. It is a type of heterocyclic compound, containing both benzene and thiophene rings. [1]Benzothieno[3,2-b]quinoline has potential applications in organic electronics, as it has been studied for use in organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs). Benzothieno[3,2-b]quinoline has been the subject of research due to its high charge-carrier mobility and the tunability of its electronic properties, making it a promising candidate for use in electronic devices. Its synthetic accessibility and stability under ambient conditions also make it an attractive candidate for organic electronics research and application.

Upstream product

• 191031-07-9 3-hydroxy-benzo[b]thiophene-2-carboxylic acid 
• 529-23-7 o-aminobenzaldehyde 
• 612-96-4 2-Phenylquinoline 
• 96907-90-3 3-chloro-2-benzothiophene 
• 62-53-3 aniline 
• 35771-74-5 11-chloro[1]benzothieno[3,2-b]quinoline 
• 7031-27-8 (phenylthio)acetic acid chloride 
• 58585-17-4 11-Oxo-5,11-dihydro-benzothieno<3,2-b><1>chinolin 
• 118-92-3 anthranilic acid 
• 77705-59-0 2-(2-(phenylthio)acetamido)benzoic acid 
• 655-15-2 2-bromo-2'-fluoroacetophenone 
• 103-04-8 (phenylthio)acetic acid 
• 10135-00-9 3-bromobenzo[b]thiophene-2-carbaldehyde 
• 191171-55-8 2-anilineboronic acid pinacol ester 

Relevant articles and documents

Benzothienoquinolines: New one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides

In this work, we were able to obtain the benzothieno[3,2-b]quinoline 1 and benzothieno[2,3-c]quinoline 2 using a new one-pot procedure from the reaction of the commercially available 3-bromobenzo[b]thiophene-2-carbaldehyde with 2-aminophenylpinacolborane under Suzuki coupling conditions using a stereochemically hindered ligand, 2-(cyclohexylphosphane)biphenyl and Ba(OH)2·8H2O as the base. Fluorescence properties of the benzothieno[3,2-b]quinoline 1 and the benzothieno[2,3-c]quinoline 2 were studied in solvents of different polarity. Both compounds exhibit a solvent sensitive emission, compound 1 being less fluorescent (ΦF A-T) base pairs. Compound 1 is the most intercalative in salmon sperm DNA (47%) and polynucleotides (46-49% of intercalated molecules), while for compound 2, 41% is intercalated in salmon sperm DNA and only 8% in poly(dG-dC)·(dG-dC). Docking studies indicate that compound 1 interacts more strongly with DNA than compound 2, with a significant value of binding free energy in the case of intercalation. Minor groove binding is also very favourable and, probably, both mechanisms occur with a preponderance of intercalation in the case of compound 1. Overall, these results indicate that both benzothienoquinolines interact with nucleic acids by both intercalation and groove binding.

Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines

The reaction of various organozinc pivalates with anthranils provides anilines derivatives, which cyclize under acidic conditions providing condensed quinolines. Using alkenylzinc pivalates, electron-rich arylzinc pivalates or heterocyclic zinc pivalates produces directly the condensed quinolines of which several structures belong to new heterocyclic scaffolds. These N-heterocycles are of particular interest for organic light emitting diodes with their high photoluminescence quantum yields and long exciton lifetimes as well as for hole-transporting materials in methylammonium lead iodide perovskites solar cells due to an optimal band alignment for holes and a large bandgap.

A new approach to the synthesis of benzofuro[3,2-b]quinolines, benzothieno[3,2-b]quinolines and indolo[3,2-b]quinolines

Treatment of 2-hydroxy-, 2-mercapto-, and 2-ethoxycarbonylamino-benzonitriles 12 with 2-fluoro- or 2-nitrophenacylbromides 13 under alkaline conditions provided the corresponding benzofuran, benzothiophene, and indole intermediates 10, respectivelly. Nucl