21873-49-4

Basic information

• Product Name: 6-Nitroquinolin-4(1H)-one
• Synonyms: 6-Nitroquinolin-4(1H)-one
• CAS NO: 21873-49-4
• Molecular Formula: C₉H₆N₂O₃
• Molecular Weight: 190.15554
• Mol File: 21873-49-4.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 6-Nitroquinolin-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Nitroquinolin-4(1H)-one(21873-49-4)
• EPA Substance Registry System: 6-Nitroquinolin-4(1H)-one(21873-49-4)

Safety Data

• Hazardous Substances Data: 21873-49-4(Hazardous Substances Data)

Usage

General Description

6-Nitroquinolin-4(1H)-one is a chemical compound with the molecular formula C9H6N2O3. It is a member of the quinoline family and is known for its nitro group and ketone functional groups. This chemical is often used as a building block for the synthesis of pharmaceuticals and agrochemicals. It also serves as an intermediate in the production of various organic compounds. 6-Nitroquinolin-4(1H)-one has applications in the fields of medicinal chemistry, drug development, and materials science due to its unique chemical properties and reactivity.

Upstream product

• 103514-53-0 ethyl 6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 78596-42-6 ethyl α-ethoxycarbonyl-β-(4-nitroanilino)acrylate 
• 100-01-6 4-nitro-aniline 
• 529-37-3 4(1H)-quinolinone 
• 122-51-0 orthoformic acid triethyl ester 
• 141-82-2 malonic acid 
• 25063-45-0 2,2-dimethyl-5-(((4-nitrophenyl)amino)methylene)-1,3-dioxane-4,6-dione 

Downstream Products

• 188244-51-1 6-amino-1-(2-methoxy-4-methoxycarbonylbenzyl)-4-oxo-1,4-dihydroquinoline 
• 188244-74-8 6-amino-2-(2-methoxy-4-methoxycarbonylbenzyl)-1-methyl-4-oxo-1,4-dihydroquinoline 
• 188244-73-7 2-(2-methoxy-4-methoxycarbonylbenzyl)-1-methyl-6-nitro-4-oxo-1,4-dihydroquinoline 
• 188244-70-4 2-(1-hydroxy-2-methoxy-4-methoxycarbonylbenzyl)-1-methyl-6-nitro-4-oxo-1,4-dihydroquinoline 
• 188244-53-3 4-[6-(2-Cyclopentyl-acetylamino)-4-oxo-4H-quinolin-1-ylmethyl]-3-methoxy-benzoic acid 
• 188244-52-2 4-[6-(2-Cyclopentyl-acetylamino)-4-oxo-4H-quinolin-1-ylmethyl]-3-methoxy-benzoic acid methyl ester 
• 195433-30-8 4-(6-Cyclopentyloxycarbonylamino-1-methyl-4-oxo-1,4-dihydro-quinolin-2-ylmethyl)-3-methoxy-benzoic acid 
• 195433-23-9 6-cyclopentyloxycarbonylamino-2-(2-methoxy-4-methoxycarbonylbenzyl)-1-methyl-4-oxo-1,4-dihydroquinoline 
• 188244-71-5 4-[Methanesulfonyloxy-(1-methyl-6-nitro-4-oxo-1,4-dihydro-quinolin-2-yl)-methyl]-3-methoxy-benzoic acid methyl ester 
• 68771-39-1 1-methyl-6-nitro-1H-quinolin-4-one 
• 188244-50-0 1-(2-methoxy-4-methoxycarbonylbenzyl)-6-nitro-4-oxo-1,4-dihydroquinoline 

Relevant articles and documents

Further studies on bis-charged tetraazacyclophanes as potent inhibitors of small conductance Ca2+-activated K+ channels

Previously, quinolinium-based tetraazacyclophanes, such as UCL 1684 and UCL 1848, have been shown to be extraordinarily sensitive to changes in chemical structure (especially to the size of the cyclophane system) with respect to activity as potent non-peptidic blockers of the small conductance Ca 2+-activated K+ ion channels (SKCa). The present work has sought to optimize the structure of the linking chains in UCL 1848. We report the synthesis and SKCa channel-blocking activity of 29 analogues of UCL 1848 in which the central CH2 of UCL 1848 is replaced by other groups X or Y = O, S, CF2, CO, CHOH, CC, CHCH, CHMe to explore whether subtle changes in bond length or flexibility can improve potency still further. The possibility of improving potency by introducing ring substituents has also been explored by synthesizing and testing 25 analogues of UCL 1684 and UCL 1848 with substituents (NO2, NH2, CF 3, F, Cl, CH3, OCH3, OCF3, OH) in the 5, 6 or 7 positions of the aminoquinolinium rings. As in our earlier work, each compound was assayed for inhibition of the afterhyperpolarization (AHP) in rat sympathetic neurons, an action mediated by the SK3 subtype of the SK Ca channel. One of the new compounds (39, R7 = Cl, UCL 2053) is twice as potent as UCL 1848 and UCL 1684: seven are comparable in activity.

Direct C-3-alkenylation of quinolones via palladium-catalyzed C-H functionalization

An unprecedented C-3-alkenylation of quinolones was reported through palladium-catalyzed C-H functionalization with 1% catalyst loading. This method provides an efficient route to a variety of new quinolone derivatives.

Regioselective synthesis of quinolin-4-ones by pyrolysis of anilinomethylene derivatives of Meldrum's acid

Electron-rich and electron-deficient anilinomethylene derivatives of Meldrum's acid cyclize equally efficiently to quinolin-4-ones via imidoylketene intermediates under flash vacuum pyrolysis (FVP) conditions. Georg Thieme Verlag Stuttgart.