1131-68-6

Basic information

• Product Name: quinoline-2-carbaldehyde oxime
• Synonyms: quinoline-2-carbaldehyde oxime
• CAS NO: 1131-68-6
• Molecular Formula: C₁₀H₈N₂O
• Molecular Weight: 172.18332
• EINECS: 214-471-7
• Mol File: 1131-68-6.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 294.6°Cat760mmHg
• Flash Point: 132°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 0.00161mmHg at 25°C
• Refractive Index: 1.623
• CAS DataBase Reference: quinoline-2-carbaldehyde oxime(CAS DataBase Reference)
• NIST Chemistry Reference: quinoline-2-carbaldehyde oxime(1131-68-6)
• EPA Substance Registry System: quinoline-2-carbaldehyde oxime(1131-68-6)

Safety Data

• Hazardous Substances Data: 1131-68-6(Hazardous Substances Data)

Usage

General Description

Quinoline-2-carbaldehyde oxime, also known as 2-quinolylcarboxaldehyde oxime, is a chemical compound with the molecular formula C10H8N2O. It is a yellowish-brown solid that is used in organic synthesis and as a chelating agent. quinoline-2-carbaldehyde oxime is commonly used in the preparation of various quinoline derivatives and is also a key intermediate in the synthesis of pharmaceuticals, dyes, and ligands for coordination compounds. Quinoline-2-carbaldehyde oxime has been found to exhibit antimicrobial and anticancer properties, making it a valuable compound with potential therapeutic applications. Additionally, its chelating properties make it useful in metal complexation and catalysis reactions.

InChI:InChI=1/C10H8N2O/c13-11-7-9-6-5-8-3-1-2-4-10(8)12-9/h1-7,12H/b9-7+

Upstream product

• 91-63-4 2-methylquinoline 
• 540-80-7 tert.-butylnitrite 
• 5470-96-2 quinoline 2-carbaldehyde 

Downstream Products

• 5760-20-3 2-aminomethylquinoline 
• 1436-43-7 quinoline-2-carbonitrile 

Relevant articles and documents

From cyclopentadiene to isoxazoline-carbocyclic nucleosides; Synthesis of highly active inhibitors of influenza a virus H1N1

The synthesis of isoxazolino-carbocyclic nornucleosides incorporating a quinoline moiety was tuned through nitrosocarbonyl intermediate chemistry, and a range of adenine analogues were attained through the linear construction of purine heterocyclic rings. The synthesis hinges on exo-selective 1,3-dipolar cycloaddition of quinolinenitrile oxide to the 2,3-oxazanorborn-5-enes and simple elaboration of the cycloadducts. The nucleoside derivatives were initially tested for their inhibitory activity against a variety of viruses, including HBV, PTV and Flu A virus H1N1. High antiviral activities were found for compounds 22aA and 22bA in the case of Flu A H1N1. The synthesis of nornucleosides incorporating a quinoline moiety was tuned through the application of nitrosocarbonyl group chemistry. The synthesis hinges on exo-selective 1,3-dipolar cycloaddition of quinolinenitrile oxide to 2,3-oxazanorborn-5-enes and elaboration of the cycloadducts. The nucleosides were tested as inhibitors of a variety of viruses and some were found highly active against Flu A H1N1. Copyright

The mechanism of the (bispidine)copper(ii)-catalyzed aziridination of styrene: A combined experimental and theoretical study

Experimental and DFT-based computational results on the aziridination mechanism and the catalytic activity of (bispidine)copper(I) and -copper(II) complexes are reported and discussed (bispidine = tetra- or pentadentate 3,7-diazabicyclo[3.1.1]-nonane derivative with two or three aromatic N donors in addition to the two tertiary amines). There is a correlation between the redox potential of the copper(II/I) couple and the activity of the catalyst. The most active catalyst studied, which has the most positive redox potential among all (bispidine)-copper(II) complexes, performs 180 turnovers in 30 min. A detailed hybrid density functional theory (DFT) study provides insight into the structure, spin state, and stability of reactive intermediates and transition states, the oxidation state of the copper center, and the denticity of the nitrene source. Among the possible pathways for the formation of the aziridine product, the stepwise formation of the two N-C bonds is shown to be preferred, which also follows from experimental results. Although the triplet state of the catalytically active copper nitrene is lowest in energy, the two possible spin states of the radical intermediate are practically degenerate, and there is a spin crossover at this stage because the triplet energy barrier to the singlet product is exceedingly high.

Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO

A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.

Copper(ii)-promoted direct conversion of methylarenes into aromatic oximes

A simple and efficient catalytic system for direct conversion of methylarenes into aromatic oximes has been developed, with Cu(OAc)2 as catalyst, NHPI (N-Hydroxyphthalimide) as additive, TBN (tert-butyl nitrite) as both the nitrogen source and the oxidant. This process proceeds under mild conditions, tolerates a wide range of substrates, affording the targeted aromatic oximes in 63-86% yields.