18441-61-7

Usage

Uses

Used in Dye and Pigment Production:
2,4,8-Trimethylquinoline is utilized as an intermediate in the production of dyes and pigments, contributing to the coloration and stability of various products.
Used in Pharmaceutical Synthesis:
It serves as a key intermediate in the synthesis of pharmaceuticals, playing a crucial role in the development of new medications.
Used in Agrochemical Synthesis:
2,4,8-Trimethylquinoline is also used in the synthesis of agrochemicals, aiding in the creation of products for agricultural applications.
Used as an Additive in Lubricating Oils:
In the lubrication industry, it functions as an additive to enhance the performance and longevity of lubricating oils.
Used as a Corrosion Inhibitor:
In petroleum and metalworking industries, 2,4,8-Trimethylquinoline acts as a corrosion inhibitor, protecting materials from degradation.
Used in Materials Science:
It has potential applications in materials science, where it can contribute to the development of new materials with specific properties.
Used in Fragrance and Flavor Production:
2,4,8-Trimethylquinoline is a component in the production of fragrances and flavors, adding to the sensory characteristics of various consumer products.

InChI:InChI=1/C12H13N/c1-8-5-4-6-11-9(2)7-10(3)13-12(8)11/h4-7H,1-3H3

Upstream product

• 107-21-1 ethylene glycol 
• 67-64-1 acetone 
• 95-53-4 o-toluidine 
• 74-86-2 acetylene 
• 85336-17-0 5-tert-butyl-2-methylaniline 
• 123-54-6 acetylacetone 
• 123-63-7 paracetaldehyde 
• 75924-41-3 4-(o-tolylamino)pent-3-en-2-one 
• 67-56-1 methanol 
• 611-32-5 8-methylquinoline 
• 109540-60-5 2-Methyl-6-((E)-1-methyl-but-2-enyl)-phenylamine 

Relevant academic research and scientific papers

Corrigendum: Organo-Photoredox Catalyzed Oxidative Dehydrogenation of N-Heterocycles (Chemistry - A European Journal, (2017), 23, 57, (14167-14172), 10.1002/chem.201703642)

The authors have been alerted to an error that was unfortunately missed at the time of publication. Table was duplicated with Table 4. The correct version of Table 2 is shown below. The authors apologise for any inconvenience caused. Organo-photoredox catalyzed oxidative dehydrogenation of tetrahydroquinolines (THQ).[a,b] (Table presented.) [a] Reaction conditions: 1 (0.5 mmol), rose bengal (1.0 mol %), N,N-dimethylacetamide (2.0 mL), open air atmosphere under visible-light irradiation at room temperature for 24 h. [b] Isolated yields. [c] 0.1 mol % of photoredox catalyst for 28 h.

Organo-Photoredox Catalyzed Oxidative Dehydrogenation of N-Heterocycles

We report here for the first time the catalytic oxidative dehydrogenation of N-heterocycles by a visible-light organo-photoredox catalyst with low catalyst loading (0.1–1 mol %). The reaction proceeds efficiently under base- and additive-free conditions with ambient air at room temperature. The utility of this benign approach is demonstrated by the synthesis of various pharmaceutically relevant N-heteroarenes such as quinoline, quinoxaline, quinazoline, acridine, and indole.

Structure-Activity Relationship for Small Molecule Inhibitors of Nicotinamide N-Methyltransferase

Nicotinamide N-methyltransferase (NNMT) is a fundamental cytosolic biotransforming enzyme that catalyzes the N-methylation of endogenous and exogenous xenobiotics. We have identified small molecule inhibitors of NNMT with >1000-fold range of activity and developed comprehensive structure-Activity relationships (SARs) for NNMT inhibitors. Screening of N-methylated quinolinium, isoquinolinium, pyrididium, and benzimidazolium/benzothiazolium analogues resulted in the identification of quinoliniums as a promising scaffold with very low micromolar (IC50 à 1 μM) NNMT inhibition. Computer-based docking of inhibitors to the NNMT substrate (nicotinamide)-binding site produced a robust correlation between ligand-enzyme interaction docking scores and experimentally calculated IC50 values. Predicted binding orientation of the quinolinium analogues revealed selective binding to the NNMT substrate-binding site residues and essential chemical features driving protein-ligand intermolecular interactions and NNMT inhibition. The development of this new series of small molecule NNMT inhibitors direct the future design of lead drug-like inhibitors to treat several metabolic and chronic disease conditions characterized by abnormal NNMT activity.

Simple and Clean Photo-induced Methylation of Heteroarenes with MeOH

Heteroarene methylation utilizing a cheap and safe methylation source without involving transition metals represents an important yet challenging objective. Here, a simple and clean catalyst-free protocol for the methylation of various heteroarenes (including six- and five-membered types) is described under light irradiation. This protocol employs cheap, readily available, and abundant MeOH as both the solvent and the methylation source. It was found that adding dichloromethane (DCM) as a co-solvent could significantly increase the yield of the methylation products. Heteroarenes bearing various functional groups could be methylated and tri-deuteromethylated successfully. Deuterium labeling studies suggested that the newly generated methyl group in the products consisted of two hydrogens from the methyl group and one hydrogen from the OH group in MeOH.

INTRAMOLECULAR CATALYTIC CYCLIZATION OF SUBSTITUTED 2-ALKENYLANILINES

A study was carried out on the effect of the nature and structure of the substituent in the aromatic ring of 2-(1-methyl-2-butenyl)anilines on the direction and structural selectivity of the their intramolecular cyclization to derivatives of quinoline and indole by the action of catalytic amounts of PdCl2 or PdCl2-(DMSO)n complexes.