233-04-5

Basic information

• Product Name: Thieno[2,3-c]quinoline (8CI,9CI)
• Synonyms: Thieno[2,3-c]quinoline (8CI,9CI)
• CAS NO: 233-04-5
• Molecular Formula: C11H7NS
• Molecular Weight: 185.24498
• Product Categories: THIENOPYRIDINE
• Mol File: 233-04-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 88-89 °C
• Boiling Point: 354.8±15.0 °C(Predicted)
• Appearance: /
• Density: 1.319±0.06 g/cm3(Predicted)
• PKA: 4.47±0.30(Predicted)
• CAS DataBase Reference: Thieno[2,3-c]quinoline (8CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Thieno[2,3-c]quinoline (8CI,9CI)(233-04-5)
• EPA Substance Registry System: Thieno[2,3-c]quinoline (8CI,9CI)(233-04-5)

Safety Data

• Hazardous Substances Data: 233-04-5(Hazardous Substances Data)

Upstream product

• 67482-48-8 3-chlorothiophene-2-carboxaldehyde 
• 191171-55-8 2-anilineboronic acid pinacol ester 
• 28322-50-1 2-diazo-1-phenyl-2-(phenylsulfonyl)ethan-1-one 
• 96919-49-2 3-(o-aminophenyl)thiophene 
• 615-36-1 2-bromoaniline 
• 37942-07-7 3,5-di-tert-butyl-2-hydroxybenzaldehyde 
• 773872-99-4 [2-(3-thienyl)phenyl]methanol 
• 6630-33-7 ortho-bromobenzaldehyde 
• 1618650-52-4 3-(2-(azidomethyl)phenyl)thiophene 
• 99902-03-1 2-(thien-3-yl)benzaldehyde 
• 99902-04-2 2-(3'-thiophene)benzyl bromide 
• 614-76-6 N-acetyl-2-bromoaniline 
• 4347-31-3 2-formylthiophene-3-boronic acid 

Relevant articles and documents

Metal-free tandem carbene N-H insertions and C-C bond cleavages

A metal-free C-H [5 + 1] annulation reaction of 2-arylanilines with diazo compounds has been achieved, giving rise to two types of prevalent phenanthridines via highly selective C-C cleavage. Compared to the simple N-H insertion manipulation of diazo, this method elegantly accomplishes a tandem N-H insertion/SEAr/C-C cleavage/aromatization reaction, and the synthetic utility of this new transformation is exemplified by the succinct syntheses of trisphaeridine and bicolorine alkaloids. This journal is

Cascade C-C and C-N Bond Formation: A Straightforward Synthesis of Phenanthridines and Fused Quinolines

A Pd-catalyzed cascade process has been developed for the synthesis of quinoline and phenanthridine derivatives from various β-chloro α,β-unsaturated aldehydes and 2-chloroaryl aldehydes, respectively, in good to high yields. The reaction proceeds through Pd-catalyzed cascade carbon-carbon and carbon-nitrogen bond formation in a single reaction vessel. The requisite β-chloro α,β-unsaturated aldehydes were efficiently synthesized from their corresponding carbonyl compounds. The use of the ligand Sphos with Pd(OAc)2 is crucial for the successful implementation of the present cascade process. This synthetic protocol is also applied for the gram-scale synthesis of a trispheridine alkaloid.

The First Synthesis of Thienoisoquinolines and an Improved Synthesis of Phenanthridine and Thienoquinolines through Pd(0) Catalyzed Coupling of ortho-Formylarylboronic Acids with Functionalized Aryl Halides

All three isomeric hitherto unknown thienoisoquinolines have been synthesized in high yields by the Pd(0)-catalyzed coupling of 2-formylbenzeneboronic acid with t-butyl-N-(ortho-halothienyl)carbamates.When 2-bromoacetanilide, instead of 2-bromoaniline, was coupled with ortho-formylarylboronic acids under Pd-catalysis, phenanthridine and thienoquinolines were obtained in improved yields. Total assignments of 1H nmr spectra of thienoisoquinolines and thienoquinolines are reported.Assignments are based on high resolution 300 MHz 1H nmr spectra, two-dimentional 1H-13C chemical shift correlation spectra and one-dimentional INADEQUATE 13C nmr spectroscopy.