103040-78-4

Basic information

• Product Name: 4-AMINO-7-METHOXYLQUINOLINE
• Synonyms: 4-AMINO-7-METHOXYLQUINOLINE;4-AMINO-7-METHOXYQUINOLINE;7-methoxyquinolin-4-amine;7-methoxy-4-Quinolinamine
• CAS NO: 103040-78-4
• Molecular Formula: C₁₀H₁₀N₂O
• Molecular Weight: 174.2
• EINECS: 200-589-5
• Mol File: 103040-78-4.mol

Chemical Properties

• Boiling Point: 369.649 °C at 760 mmHg
• Flash Point: 177.357 °C
• Appearance: /
• Density: 1.218 g/cm³
• Vapor Pressure: 1.17E-05mmHg at 25°C
• Refractive Index: 1.664
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-AMINO-7-METHOXYLQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-7-METHOXYLQUINOLINE(103040-78-4)
• EPA Substance Registry System: 4-AMINO-7-METHOXYLQUINOLINE(103040-78-4)

Safety Data

• Hazardous Substances Data: 103040-78-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Amino-7-methoxyquinoline is used as a potential anti-malarial drug due to its unique chemical structure and activity against the Plasmodium parasite, which causes malaria.
Used in Research and Diagnostics:
As a fluorescent probe, 4-amino-7-methoxyquinoline is utilized for the detection and analysis of various biological substances, offering a valuable tool in life sciences and medical research.
Used in Chemical Synthesis:
4-Amino-7-methoxyquinoline serves as a precursor in the synthesis of other bioactive compounds, contributing to the development of new pharmaceuticals and chemical products.
Used in Antimicrobial Applications:
4-AMINO-7-METHOXYLQUINOLINE is employed as an antimicrobial agent, leveraging its ability to inhibit the growth of certain bacteria, thereby offering potential in the treatment of bacterial infections.
Used in Antiparasitic Applications:
4-Amino-7-methoxyquinoline is used as an antiparasitic agent, targeting parasites that cause various diseases, thus expanding its potential use in the medical field for treating parasitic infections.

InChI:InChI=1/C10H10N2O/c1-13-7-2-3-8-9(11)4-5-12-10(8)6-7/h2-6H,1H3,(H2,11,12)

Upstream product

• 103754-61-6 7-methoxy-4-nitro-quinoline 
• 49612-23-9 7-methoxy-4-hydrazinoquinoline 
• 536-90-3 m-Anisidine 
• 56881-19-7 Diethyl 2-<(3-methoxyphenylamino)methylene>malonate 
• 63463-15-0 ethyl 4-hydroxy-7-methoxyquinoline-3-carboxylate 
• 28027-17-0 4-hydroxy-7-methoxy-3-quinoline carboxylic acid 
• 82121-05-9 4-hydroxy-7-methoxyquinoline 
• 68500-37-8 4-chloro-7-methoxyquinoline 
• 213699-52-6 5-[[(3-methoxyphenyl)amino]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione 

Downstream Products

• 220843-92-5 1-(4-N,N-dimethylaminophenyl)-3-(7-methoxy)quinolin-4-ylurea hydrochloride 

Relevant articles and documents

Structure-activity relationships for ferriprotoporphyrin IX association and β-hematin inhibition by 4-aminoquinolines using experimental and ab initio methods

In order to probe structure-activity relationships of association with ferriprotoporphyrin IX (log K) and inhibition of β-hematin formation, a series of 4-aminoquinolines with varying substituents at the 7-position (X) have been synthesized. These have been further elaborated by introduction of two different R groups on the 4-amino nitrogen atom in the form of methyl (R = Me) and ethylamine (R = EtNH2) side chains. Data for a previously investigated series containing an N,N-diethyl-ethylamine side chain were also compared with the findings of this study. Experimentally, log K values for the simple 4-aminoquinoline series (R = H) were found to correlate with the hydrophobicity constant (π) of the group X. The log K values for the series with R = Me and EtNH2 were found to correlate with those of the series with R = H. The log of the 50% β-hematin inhibitory activity (log BHIA50) was found to correlate with log K and either meta (σm) or para (σp) Hammett constants for the series with R = Me and EtNH2, but not the simple series with R = H. To further improve predictability, correlations with ab initio electrostatic parameters, namely Mulliken and CHelpG charges were investigated. The best correlations were found with CHelpG charges which indicated that log K values can be predicted from the charges on atom H-8 and the group X in the quinolinium species computed in vacuum, while log BHIA50 values can be predicted from the CHelpG charges on C-7, C-8 and N-1 for the neutral species in vacuum. These correlations indicate that association and inhibition of β-hematin formation are separately determined. They also suggest that electron withdrawing groups at the 7-position, but not necessarily hydrophobic groups are required for hemozoin inhibition. The upshot is that the correlations imply that considerably more hydrophilic hemozoin inhibitors are feasible.

Microwave-assisted synthesis of 4-quinolylhydrazines followed by nickel boride reduction: a convenient approach to 4-aminoquinolines and derivatives

Nickel(II) chloride/sodium borohydride combination was employed for the reduction of 4-hydrazinoquinoline derivatives to the corresponding anilines. This reductive protocol was efficiently applied for the reductive cleavage of monosubstituted hydrazines. We described herein the microwave-assisted synthesis of 4-hydrazinoquinolines, which furnished a high yielding and rapid two-step procedure for the synthesis, under mild conditions, of 4-aminoquinolines as antimalarial precursors.