54232-06-3

Basic information

• Product Name: 6-methoxy-2-methyl-8-nitroquinoline
• Synonyms: 2-Methyl-6-methoxy-8-nitroquinoline; 6-Methoxy-2-methyl-8-nitroquinoline
• CAS NO: 54232-06-3
• Molecular Formula: C₁₁H₁₀N₂O₃
• Molecular Weight: 218.2087
• Mol File: 54232-06-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 373°C at 760 mmHg
• Flash Point: 179.4°C
• Density: 1.292g/cm³
• Vapor Pressure: 1.98E-05mmHg at 25°C
• Refractive Index: 1.631
• CAS DataBase Reference: 6-methoxy-2-methyl-8-nitroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methoxy-2-methyl-8-nitroquinoline(54232-06-3)
• EPA Substance Registry System: 6-methoxy-2-methyl-8-nitroquinoline(54232-06-3)

Safety Data

• Hazardous Substances Data: 54232-06-3(Hazardous Substances Data)

Usage

General Description

6-methoxy-2-methyl-8-nitroquinoline is a chemical compound with the molecular formula C11H10N2O3. It is a member of the quinoline family, which are heterocyclic aromatic compounds commonly used in the pharmaceutical and agrochemical industries. This specific compound is characterized by the presence of a methoxy group at the 6 position, a methyl group at the 2 position, and a nitro group at the 8 position on the quinoline ring. Its chemical structure and properties make it useful for various applications, including as a building block in the synthesis of pharmaceutical drugs, agrochemicals, and other organic molecules. Additionally, it has been studied for its potential biological activities and interactions with other molecules.

Upstream product

• 123-63-7 paracetaldehyde 
• 96-96-8 4-methoxy-2-nitroaniline 
• 123-73-9 crotonaldehyde 
• 75-07-0 acetaldehyde 

Downstream Products

• 316124-68-2 6-methoxy-8-nitro-2-[(E)-2-phenyl-1-ethenyl]quinoline 
• 61895-33-8 5,8-Dinitro-6-methoxy-2-methylchinolin 
• 181530-10-9 [6-Ethoxycarbonylmethoxy-2-methyl-8-(toluene-4-sulfonylamino)-quinolin-5-yl]-acetic acid ethyl ester 
• 181530-14-3 (E)-3-[6-Methoxy-2-methyl-8-(toluene-4-sulfonylamino)-quinolin-5-yl]-acrylic acid ethyl ester 
• 151751-11-0 [5-Bromo-2-methyl-8-(toluene-4-sulfonylamino)-quinolin-6-yloxy]-acetic acid ethyl ester 
• 181530-09-6 ethyl [(2-methyl-8-p-toluenesulfonylaminoquinolin-6-yloxy)acetate] 
• 151606-29-0 2-methyl-8-(4-toluenesulfonamido)-6-quinolyloxyacetic acid 
• 181530-13-2 N-(5-Iodo-6-methoxy-2-methyl-quinolin-8-yl)-4-methyl-benzenesulfonamide 
• 181530-08-5 N-(5-Bromo-6-hydroxy-2-methyl-quinolin-8-yl)-4-methyl-benzenesulfonamide 
• 157890-02-3 N-(6-methoxy-2-methyl-8-quinolyl)-(4-methylbenzene)sulfonamide 
• 151751-12-1 2-methyl-6-hydroxy-8-(p-toluenesulfonamido)quinoline 
• 316124-89-7 ethyl 2-(2-[(E)-2-phenyl-1-ethenyl]-6-quinolyloxy-8-p-toluenesulfonamido)acetate 
• 316124-90-0 ethyl 2-[2-(2-methyl-1-propenyl)-6-quinolyloxy-8-p-toluenesulfonamido]acetate 
• 316124-91-1 ethyl 2-(2-isobutyl-6-quinolyloxy-8-p-toluenesulfonamido)acetate 

Relevant articles and documents

A Tetrakisquinoline Analog of Calcium Indicator Quin2 for Fluorescence Detection of Cd2+

Quin2 (2-{2-[bis(carboxymethyl)amino-5-methylphenoxy]methyl}-6-methoxy-8-[bis(carboxymethyl)amino]quinoline) is a well-known fluorescent Ca2+ indicator. In this study, we replaced its four carboxy groups with quinolines and deleted a methyl group on the benzene ring to afford TQquin2 [N,N,N',N'-tetrakis(2-quinolylmethyl)-8-amino-2-(2-aminophenoxy)methyl-6-methoxyquinoline]. In methanol solution, TQquin2 exhibited fluorescence enhancement toward Cd2+ with excellent selectivity.

Novel quinolinequinone antitumor agents: Structure-metabolism studies with NAD(P)H:quinone oxidoreductase (NQO1)

A series of quinolinequinones bearing various substituents has been synthesized, and the effects of substituents on the metabolism of the quinones by recombinant human NAD(P)H:quinone oxidoreductase (hNQO1) was studied. A range of quinolinequinones were selected for study, and were specifically designed to probe the effects of aryl substituents at C-2. A range of 28 quinolinequinones 2-29 was prepared using three general strategies: the palladium(0) catalyzed coupling of 2-chloroquinolines, the classical Friedlaender synthesis and the double-Vilsmeier reaction of acetanilides. One example of an isoquinolinequinone 30 was also prepared, and the reduction potentials of the quinones were measured by cyclic voltammetry. For simple substituents R2 at the quinoline 2-position, the rates of quinone metabolism by hNQO1 decrease for R2=Cl>H～Me>Ph. For aromatic substituents, the rate of reduction decreases dramatically for R 2=Ph>1-naphthyl>2-naphthyl>4-biphenyl. Compounds containing a pyridine substituent are the best substrates, and the rates decrease as R 2=4-pyridyl>3-pyridyl>2-pyridyl>4-methyl-2-pyridyl>5- methyl-2-pyridyl. The toxicity toward human colon carcinoma cells with either no detectable activity (H596 or BE-WT) or high NQO1 activity (H460 or BE-NQ) was also studied in representative quinones. Quinones that are good substrates for hNQO1 are more toxic to the NQO1 containing or expressing cell lines (H460 and BE-NQ) than the NQO1 deficient cell lines (H596 and BE-WT).