73568-43-1

Basic information

• Product Name: 7-CHLORO-2-HYDROXYQUINOLINE-3-CARBALDEHYDE
• Synonyms: 7-CHLORO-2-HYDROXYQUINOLINE-3-CARBALDEHYDE;7-chloro-2-oxo-1H-quinoline-3-carbaldehyde
• CAS NO: 73568-43-1
• Molecular Formula: C₁₀H₆ClNO₂
• Molecular Weight: 207.61
• Mol File: 73568-43-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 445°C at 760 mmHg
• Flash Point: 222.9°C
• Appearance: /
• Density: 1.497g/cm³
• Vapor Pressure: 4.09E-08mmHg at 25°C
• Refractive Index: 1.69
• CAS DataBase Reference: 7-CHLORO-2-HYDROXYQUINOLINE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-CHLORO-2-HYDROXYQUINOLINE-3-CARBALDEHYDE(73568-43-1)
• EPA Substance Registry System: 7-CHLORO-2-HYDROXYQUINOLINE-3-CARBALDEHYDE(73568-43-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 73568-43-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H6ClNO2/c11-8-2-1-6-3-7(5-13)10(14)12-9(6)4-8/h1-5H,(H,12,14)

Upstream product

• 108-42-9 3-chloro-aniline 
• 588-07-8 3-Chloroacetanilide 
• 78708-05-1 (E)-N-(3-Chloro-phenyl)-3-dimethylamino-2-formyl-acrylamide 
• 78708-18-6 (E)-N-(3-Chloro-phenyl)-2-formyl-3-hydroxy-acrylamide 
• 73568-33-9 2,7-dichloro-quinoline-3-carbaldehyde 

Downstream Products

• 1438397-61-5 1-allyl-7-chloro-3-(3,5-dimethyl-1,7-bis(3-chlorophenyl)-1,4-dihydro-1H-dipyrazolo[3,4-b:4'3'-e]pyran-4-yl)quinoline-2-one 
• 1438397-60-4 1-allyl-7-chloro-3-(3,5-dimethyl-1,7-bis(2-chlorophenyl)-1,4-dihydro-1H-dipyrazolo[3,4-b:4'3'-e]pyran-4-yl)quinoline-2-one 
• 1438397-59-1 1-allyl-7-chloro-3-(3,5-dimethyl-1,7-diphenyl-1,4-dihydro-1H-dipyrazolo[3,4-b:4'3'-e]pyran-4-yl)quinoline-2-one 
• 1438397-54-6 4,4'-[(1-allyl-7-chloroquinolin-2-one)methylene]bis[3-methyl-1-(2,5-dichlorophenyl)-1H-pyrazol-5-ol] 
• 1438397-53-5 4,4'-[(1-allyl-7-chloroquinolin-2-one)methylene]bis[3-methyl-1-(3-chlorophenyl)-1H-pyrazol-5-ol] 
• 1438397-52-4 4,4'-[(1-allyl-7-chloroquinolin-2-one)methylene]bis[3-methyl-1-(2-chlorophenyl)-1H-pyrazol-5-ol] 
• 1438397-51-3 4,4'-[(1-allyl-7-chloroquinolin-2-one)methylene]bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) 
• 1438397-46-6 1-allyl-7-chloro-3-{(Z)-[1-(2,5-dichlorophenyl)-3-methyl-1,5-dihydro-4H-pyrazol-5-one-4-ylidene]methyl}quinolin-2(1H)-one 
• 1438397-45-5 1-allyl-7-chloro-3-{(Z)-[1-(3-chlorophenyl)-3-methyl-1,5-dihydro-4H-pyrazol-5-one-4-ylidene]methyl}quinolin-2(1H)-one 
• 1438397-44-4 1-allyl-7-chloro-3-{(Z)-[1-(2-chlorophenyl)-3-methyl-1,5-dihydro-4H-pyrazol-5-one-4-ylidene]methyl}quinolin-2(1H)-one 
• 1438397-43-3 1-allyl-7-chloro-3-[(Z)-(3-methyl-1-phenyl-1,5-dihydro-4H-pyrazol-5-one-4-ylidene)methyl]quinolin-2(1H)-one 

Relevant articles and documents

Antimicrobial activity of quinoline-based hydroxyimidazolium hybrids

Eight quinoline-based hydroxyimidazolium hybrids 7a-h were prepared and evaluated in vitro against a panel of clinically important fungal and bacterial pathogens, including mycobacteria. Hybrid compounds 7c-d showed remarkable antifungal activity against Cryptococcus neoformans with a minimum inhibitory concentration (MIC) value of 15.6 μg/mL. Against other opportunistic fungi such as Candida spp. and Aspergillus spp., these hybrids showed MIC values of 62.5 μg/mL. Regarding their antibacterial activity, all the synthetic hybrids demonstrated little inhibition of Gram-negative bacteria (MIC ≥50 μg/mL), however, hybrid 7b displayed >50% inhibition against Klebsiella pneumoniae at 20 μg/mL and full inhibition at 50 μg/mL. Moreover, this hybrid was shown to be a potent anti-staphylococcal molecule, with a MIC value of 2 μg/mL (5 μM). In addition, hybrid 7h also demonstrated inhibition of Staphylococcus aureus at 20 μg/mL (47 μM). Hybrids 7a and 7b were the most potent against Mycobacterium tuberculosis H37Rv with MIC values of 20 and 10 μg/mL (46 and 24 μM), respectively. The 7b hybrid demonstrated high selectivity in killing S. aureus and M. tuberculosis H37Rv in comparison with mammalian cells (SI >20), and thus it can be considered a hit molecule for mechanism of action studies and the exploration of related chemical space.

Microwave-assisted synthesis of diversely substituted quinoline-based dihydropyridopyrimidine and dihydropyrazolopyridine hybrids

An efficient, catalyst-free, and one-pot three-component procedure for the synthesis of novel and nitrogen rich dihydropyrido[2, 3-d]pyrimidines and dihydro-1H-pyrazolo[3, 4-b]pyridines bearing a quinoline pharmacophore fragment is provided. Reactions proceeded in DMF under microwave irradiation of three-component mixtures of formyl-quinoline derivatives, primary heterocyclic amines and cyclic 1, 3-diketones. Interestingly, when conventional heating at reflux was used for the starting 5-amino-1-phenylpyrazole, the corresponding aromatized pyrazolopyridines were obtained as the main products. Single crystal X-ray analysis confirmed unequivocally the structure of both the dihydro- and aromatized products.

Novel quinoline-imidazolium adducts via the reaction of 2-oxoquinoline-3-carbaldehyde and quinoline-3-carbaldehydes with 1-butyl-3-methylimidazolium chloride [BMIM][Cl]

A library of hydroxyquinolin-3-ylmethylimidazolium adducts were prepared in high yields from the reaction of [BMIM][Cl] with various substituted quinoline-3-carbaldehydes and 2-oxoquinoline-3-carbaldehydes under mild conditions by using sodium acetate in MeCN under ultrasound irradiation. The use of sodium acetate and imidazolium chloride was crucial for the success of these CC bond forming reactions. Attempted coupling with thiazolium bromide led instead to quinoline-3-carboxylic acid.