59394-26-2

Basic information

• Product Name: 6-CHLOROQUINOLINE-2-CARBALDEHYDE
• Synonyms: 6-CHLOROQUINOLINE-2-CARBALDEHYDE;6-chloroquinoline-2-carbaldehyde(SALTDATA: FREE);6-chloro-2-quinolinecarboxaldehyde;6-chloroquinaldaldehyde
• CAS NO: 59394-26-2
• Molecular Formula: C₁₀H₆ClNO
• Molecular Weight: 191.62
• Mol File: 59394-26-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: 140 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 349.3°Cat760mmHg
• Flash Point: 165°C
• Appearance: /
• Density: 1.364g/cm³
• Vapor Pressure: 4.76E-05mmHg at 25°C
• Refractive Index: 1.692
• PKA: 2.85±0.43(Predicted)
• CAS DataBase Reference: 6-CHLOROQUINOLINE-2-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLOROQUINOLINE-2-CARBALDEHYDE(59394-26-2)
• EPA Substance Registry System: 6-CHLOROQUINOLINE-2-CARBALDEHYDE(59394-26-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 59394-26-2(Hazardous Substances Data)

Usage

Description

6-Chloroquinoline-2-carbaldehyde is an organic compound that serves as a key intermediate in the synthesis of various quinoline-based derivatives. It possesses a chloro substituent at the 6th position and a formyl group at the 2nd position of the quinoline ring, which allows for further functionalization and the development of bioactive molecules.

Uses

Used in Pharmaceutical Industry:
6-Chloroquinoline-2-carbaldehyde is used as a reagent for the design, synthesis, and biological evaluation of 2-substituted quinoline libraries. These libraries consist of potential antileishmanial agents, which are crucial for the development of new treatments against Leishmaniasis, a vector-borne disease caused by protozoan parasites.
Used in Drug Discovery:
6-Chloroquinoline-2-carbaldehyde is also utilized in the synthesis and biological evaluation of quinoline derivatives as HDAC (Histone Deacetylase) class I inhibitors. HDAC inhibitors are a class of compounds that modulate gene expression by altering the acetylation state of histones, which can have therapeutic potential in various diseases, including cancer and neurodegenerative disorders. By targeting HDAC class I, these quinoline derivatives may offer novel therapeutic options for the treatment of these conditions.

InChI:InChI=1/C10H6ClNO/c11-8-2-4-10-7(5-8)1-3-9(6-13)12-10/h1-6H

Upstream product

• 106-47-8 4-chloro-aniline 
• 15644-86-7 6-chloro-2-methyl-quinolin-4-ol 
• 92-46-6 6-chloro-2-methylquinoline 

Relevant articles and documents

Iodine-catalyzed oxidative annulation: Facile synthesis of pyrazolooxepinopyrazolones: Via methyl azaarene sp3C-H functionalization

An iodine-catalyzed methyl azaarene sp3 C-H functionalization has been developed for the synthesis of a seven-membered O-heterocyclic architecture containing three different heterocyclic aromatic hydrocarbons. This method can be applied to a wide range of substituted methyl azaarenes and diverse 2,4-dihydro-3H-pyrazol-3-ones, and brings about the efficient preparation of 2,9-dihydrooxepino[2,3-c:6,5-c′]dipyrazol-3(7H)-ones in high yields with the merits of low catalyst loading, good functional group tolerance and metal-free conditions.

Facile synthesis of 1,3,4-oxadiazoles via iodine promoted oxidative annulation of methyl-azaheteroarenes and hydrazides

An oxidative sp3 C–H bond of methyl-azaheteroarenes protocol was reported for the synthesis of 1,3,4-oxadiazoles via [4 + 1] annulation with hydrazides. This protocol enables 1,3,4-oxadiazole and quinoline linked diheterocycles via selective oxidation of sp3 C–H bond of methyl-azaheteroarenes in the presence of I2-DMSO. The reaction has a broad substrate scope and good functional group tolerance for methyl-azaheteroarenes and hydrazides.

Metal- and radical-free aerobic oxidation of heteroaromatic methanes: An efficient synthesis of heteroaromatic aldehydes

A metal-free and radical-free synthesis of heteroaromatic aldehydes was developed through aerobic oxidation of methyl groups in an I2/DMSO/O2 catalytic system. Under the reaction conditions, various functional groups such as methoxy, aldehyde, ester, nitro, amide, and halo (F, Cl, Br) groups were well tolerated. The bioactive compounds like chlorchinaldin derivative and papaverine were also oxidized to the corresponding aldehydes and ketones. This reaction provided an efficient method for preparing the valuable heteroaromatic aldehydes.