5541-67-3

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
5-methylquinolin-8-ol is utilized as an intermediate in the synthesis of pharmaceuticals and agrochemicals, leveraging its chemical properties to contribute to the development of new drugs and pesticides. Its role in these industries is crucial for creating effective treatments and protection agents.
Used in Dye and Pigment Production:
In the dye and pigment industry, 5-methylquinolin-8-ol is employed for the production of various dyes and pigments. Its chemical structure allows it to impart color and stability to these products, making it a valuable component in this sector.
Used in Organic Synthesis:
5-methylquinolin-8-ol is also used in organic synthesis processes, where it serves as a building block for the creation of more complex organic compounds. Its versatility in chemical reactions makes it a useful tool in the synthesis of a wide range of organic molecules.
Used as a Chelating Agent in Analytical Chemistry:
5-methylquinolin-8-ol has been investigated for its potential as a chelating agent in analytical chemistry. Its ability to form complexes with metal ions can be harnessed for various analytical techniques, enhancing the selectivity and sensitivity of these methods.
Used as a Corrosion Inhibitor in Metal Surface Treatment:
In the field of metal surface treatment, 5-methylquinolin-8-ol has been studied for its effectiveness as a corrosion inhibitor. Its application helps protect metal surfaces from degradation, extending the lifespan and performance of metal components in various industries.

InChI:InChI=1/C10H9NO/c1-7-4-5-9(12)10-8(7)3-2-6-11-10/h2-6,12H,1H3

Upstream product

• 2598-30-3 8-hydroxyquinoline-5-carbaldehyde 
• 95-84-1 3-amino-4-hydroxytoluene 
• 56-81-5 glycerol 
• 126403-57-4 8-methoxy-5-methyl-quinoline 
• 17012-44-1 chloro-5 methoxy-8 quinoleine 
• 148-24-3 8-quinolinol 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 107-02-8 acrolein 
• 119-33-5 4-methyl-2-nitrophenol 

Downstream Products

• 110194-20-2 5,5'-dimethyl-7,7'-methanediyl-bis-quinolin-8-ol 
• 73987-42-5 5-Methyl-7-hydroxymethyl-8-hydroxy-chinolin 
• 126403-57-4 8-methoxy-5-methyl-quinoline 
• 213881-39-1 8-benzenesulfonyloxy-5-methylquinoline 
• 7175-09-9 7-bromo-8-hydroxy-5-methylquinoline 
• 92951-85-4 Rh(5-methyl-8-hydroxyquinolate)(CO)(2-bromo-3,4,5,6-tetrafluorophenyldiphenylphosphine) 
• 5541-74-2 5-methyl-8-hydroxyquinoline-7-carbaldehyde 
• 1312683-42-3 N-{1-[8-(3-fluorophenyl)-5-methylquinolin-7-yl]ethyl}-9H-purin-6-amine 
• 1312685-97-4 1-[8-(3-fluorophenyl)-5-methylquinolin-7-yl]ethanamine 
• 1312685-96-3 1-[8-(3-fluorophenyl)-5-methylquinolin-7-yl]ethanone 
• 115228-71-2 8-benzoyloxy-7-benzoyloximethyl-5-methyl-quinoline 

Relevant academic research and scientific papers

Study on Relationship Between Fluorescence Properties and Structure of Substituted 8-Hydroxyquinoline Zinc Complexes

Organic light-emitting diodes (OLEDs) produced from 8-hydroxyquinoline metal complexes play a vital role in modern electroluminescent devices. In this manuscript, a series of 8-hydroxyquinoline derivatives were synthesized by different methods and their corresponding zinc metal complexes were prepared. The UV and fluorescence properties of the complexes were measured aiming to understand the effect of substituents at the quinoline ring on the fluorescence properties of the complexes. When the C-5 of 8-hydroxyquinoline was replaced by halogen group, the fluorescence emission wavelengths had been red-shifted, at the same time, blue-shifted of fluorescence emission wavelength was observed when the C-5 position of 8-hydroxyquinoline was substituted by electron-withdrawing group. When the C-4 position of 8-hydroxyquinolie was substituted by methyl or the C-5 position was substituted by sulfonic acid group, the corresponding zinc complexes had higher fluorescence intensity than 8-hydroxyquinolie zinc.

Quinoline synthesis by improved Skraup-Doebner-Von Miller reactions utilizing acrolein diethyl acetal

A robust synthetic method has been developed as an improvement to the venerable Skraup-Doebner-Von Miller reaction providing access to various quinoline products. The straightforward procedure utilizes acrolein diethyl acetal as a three-carbon annulation partner with aniline substrates in a monophasic, organic solvent-free reaction medium. Differentially substituted aniline precursors were found to be compatible with the reaction conditions and the corresponding quinoline products are isolated in moderate to good yields.

Betti reaction enables efficient synthesis of 8-hydroxyquinoline inhibitors of 2-oxoglutarate oxygenases

There is interest in developing potent, selective, and cell-permeable inhibitors of human ferrous iron and 2-oxoglutarate (2OG) oxygenases for use in functional and target validation studies. The 3-component Betti reaction enables efficient one-step C-7 functionalisation of modified 8-hydroxyquinolines (8HQs) to produce cell-active inhibitors of KDM4 histone demethylases and other 2OG oxygenases; the work exemplifies how a template-based metallo-enzyme inhibitor approach can be used to give biologically active compounds.

4,4'-bipyridine as a unidirectional switching unit for a molecular pushing motor

A chirality switch in which the intrinsic chirality of a 4,4'-bipyridine is combined with a metal-ion-induced switching principle is described. In the uncomplexed state the 4,4'-bipyridine unit, which is linked to an S,S,S,S-configured cyclic imidazole peptide, is P-configured. The addition of zinc ions leads to a rotation around the C-C bond axis of the 4,4'-bipyridine and the Misomer of the metal complex is formed. By addition of a stronger complexing agent the metal ions are removed and the switch returns to its initial position. The combination of the chirality switch with a second switching unit allows the construction of a molecular pushing motor, which is driven chemically and by light. Motor drive: The combination of the intrinsic chirality of a 4,4'-bipyridine with a metal-ion-induced switching principle leads to a metal-ion-induced chirality switch that can also be used as a basic unit for a molecular pushing motor. Rotation around the C-C bond axis of the bipyridine, which is linked to a cyclic imidazole peptide, leads to switching between P and Misomers (see scheme).

Aza-and polyaza-naphthalenly ketones useful as hiv integrase inhibitors

Certain aza- and polyaza-naphthalenyl ketones including certain quinolinyl and naphthyridinyl ketones are described as inhibitors of HIV integrase and inhibitors of HIV replication. These compounds are useful in the prevention or treatment of infection by HIV and the treatment or the delay in the onset of AIDS, as compounds or pharmaceutically acceptable salts, or as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating or delaying the onset of AIDS and methods of preventing or treating infection by HIV are also described.

A SHORT AND CONVENIENT SYNTHESIS OF 5-ALKYL SUBSTITUTED 8-HYDROXYQUINOLINES

5-Chloro-8-methoxyquinoline undergoes rapid and reversible lithium-halogen exchange reaction with alkyllithiums to yield 5-substituted derivatives indirectly, whereas the reaction with phenyllithium is slower and 5-alkyl substituted compounds are formed by the direct addition of alkyl halides.