4663-93-8

Basic information

• Product Name: Quinolinaldehyde
• Synonyms: 2,3-Pyridinedicarbaldehyde;Quinolinaldehyde;2,3-pyridine dicarboxaldehyde;pyridine-2,3-dicarbaldehyde
• CAS NO: 4663-93-8
• Molecular Formula: C₇H₅NO₂
• Molecular Weight: 135.1201
• Mol File: 4663-93-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 277.435 °C at 760 mmHg
• Flash Point: 125.795 °C
• Appearance: /
• Density: 1.275 g/cm³
• CAS DataBase Reference: Quinolinaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: Quinolinaldehyde(4663-93-8)
• EPA Substance Registry System: Quinolinaldehyde(4663-93-8)

Safety Data

• Hazardous Substances Data: 4663-93-8(Hazardous Substances Data)

Usage

General Description

Quinolinaldehyde, also known as 1H-Quinolin-2-one or 2-Quinolinol, is an aromatic organic compound derived from quinoline, classified as a heteroaromatic compound due to its structural similarities to both aldehydes and amines. It is a crystalline compound that appears as light yellow needles and has a faint, pleasant aroma. Known to be a metabolite of the amino acid tryptophan, the chemical exhibits several important applications in medicine, the synthesis of pharmaceuticals, and in biochemistry due to its antibacterial and antifungal properties. However, Quinolinaldehyde can also be a skin, eye, and respiratory irritant and handling should be done cautiously.

Upstream product

• 2050-22-8 2,3-diethyl pyridinedicarboxylate 
• 38070-79-0 2,3-bis(hydroxymethyl)pyridine 
• 605-38-9 dimethyl 2,3-pyridinedicarboxylate 

Downstream Products

• 4733-69-1 furo[3,4-b]pyridine-7(5H)-one 
• 5657-51-2 7H-furo[3,4-b]pyridin-5-one 
• 25242-45-9 5,7-diethoxy-5,7-dihydro-furo[3,4-b]pyridine 
• 25242-49-3 1,3-diethoxy-1,3-dihydro-furo[3,4-c]pyridine 
• 1256375-24-2 6,13-anthradipyridinequinone 
• 253-73-6 pyrido<2,3-d>pyridazine 

Relevant articles and documents

Coplanar tetracyclic π-excess σ2P ligands

The acid-catalyzed reactions of 5-methyl-2-phosphanylaniline (1) with dialdehydes were studied. Whereas the reaction with glyoxal provides a mixture of two 1H-1,3-benzazaphospholes, 2 and 3, by concomitant reduction of a CHO group and C-C bond cleavage, respectively, the reaction with o-phthalic dicarbaldehyde provided in excellent yield the tetracyclic planar benzazaphosphole 4, which was characterized by crystal structure analysis. The active hydrogen atoms, delivered by aromatization of a dihydrobenzazaphosphole intermediate, forms an N-CH2 bridge by reductive N-alkylation. Pyridine-2,6-dicarbaldehyde reacts analogously but not chemoselectively and, thus, gives two isomers 5 and 6. Condensation with pyridine-2,6-dicarbaldehyde afforded the bis(benzazaphosphole)pyridine pincer ligand 7, but along with 2-(benzazaphospholyl)-6-tolylpyridine (8) by partial P-C bond cleavage. The high upfield 31P NMR chemical shift of 4 compared to those of normal benzazaphospholes indicates it to be a particularly π-rich σ2P ligand. Aromatization-driven acid-catalyzed condensations of the N,P-diprimary compound 1 with dialdehydes are coupled with hydrogen transfer reactions. With glyoxal and pyridine-2,6-dicarbaldehyde this gives rise to side products, but with o-C6H4(CHO)2, high yields of 4 are obtained. π-Delocalization through the coplanar aryl rings causes high π-density at the phosphorus atom.

Synthesis of 2-Aryl-2,3-dihydro-oxazolopyrrolopyridin-5-one and 2-Aryl-2,3-dihydro-oxazolopyrrolopyridin-5-one

A variety of 2-aryl-2,3-dihydro-oxazolopyrrolopyridin-5-one and 2-aryl-2,3-dihydro-oxazolopyrrolopyridin-5-one were prepared. The absolute configuration of the chiral centers were studied thoroughly from which the structural and stereoformulea of these compounds were deduced by using nmr and microanalysis technique.