7727-09-5

Basic information

• Product Name: 2-Quinolinecarboxaldehyde, phenylhydrazone
• CAS NO: 7727-09-5
• Molecular Formula: C16H13N3
• Molecular Weight: 247.299
• Mol File: 7727-09-5.mol

Chemical Properties

• CAS DataBase Reference: 2-Quinolinecarboxaldehyde, phenylhydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Quinolinecarboxaldehyde, phenylhydrazone(7727-09-5)
• EPA Substance Registry System: 2-Quinolinecarboxaldehyde, phenylhydrazone(7727-09-5)

Safety Data

• Hazardous Substances Data: 7727-09-5(Hazardous Substances Data)

Upstream product

• 21640-66-4 1-methyl-2-(phenylhydrazono-methyl)-quinolinium; iodide 
• 100-63-0 phenylhydrazine 
• 5470-96-2 quinoline 2-carbaldehyde 
• 91-63-4 2-methylquinoline 
• 13119-76-1 2-oxo-3-quinolin-2-yl-propionic acid ethyl ester 
• 55857-35-7 (E)-N-(2-aminobenzylidene)-4-methylaniline 

Downstream Products

• 77383-58-5 3-[2]quinolyl-1,5-diphenyl-formazan 

Relevant articles and documents

Synthesis, anti-tuberculosis activity, and 3D-QSAR study of ring-substituted-2/4-quinolinecarbaldehyde derivatives

We have previously identified ring-substituted quinolines as a new structural class of anti-tuberculosis agents. In our ongoing efforts at structural optimization of this class, four series of ring-substituted-2/4-quinolinecarbaldehyde derivatives were sy

Multiple dynamics of hydrazone based compounds

Hydrazone derivatives of 2-quinolinecarboxaldehyde and 6-bromo-2-pyridinecarboxaldehyde were synthesized by sequence reactions with hydrazine derivatives. These compounds exhibited E/Z isomerization upon irradiation using a mercury lamp (250 W). The configurational changes were monitored by 1H nuclear magnetic resonance (NMR), UV-Vis and fluorescence spectroscopy. Data of concentration of the E/Z isomers versus time showed first order kinetics with constants ranging from 0.024 to 0.0799 min-1. The Z isomers were isolated by chromatographic methods and characterized by 1H NMR, UV-Vis and fluorescence spectroscopy and X-ray diffraction. The Z compounds are stable even in solution for several months. Such stability is due to a thermodynamic stabilization by the formation of an intramolecular hydrogen bond in the Z structure, which is not seen in the E configuration. Furthermore, some of the compounds were used as ligands for various metal centers (Zn2+, Co2+ and Hg2+) and their electronic properties were studied including measurements of cyclic voltammetry. The compounds studied herein allow their use as dynamic systems in dynamic combinatorial chemistry as their properties can be modulated by light, heat and the presence of metal centers. Besides, obtaining a metastable state (Z-isomer) allows the use of these compounds as photo-brakes, and therefore they can be implemented as molecular machines.