5349-78-0

Basic information

• Product Name: 4,8-DIMETHYL-2-QUINOLINOL
• Synonyms: 4,8-DIMETHYL-2-QUINOLINOL;4,8-dimethyl-1H-quinolin-2-one;4,8-dimethylcarbostyril;4,8-DIMETHYL-2-HYDROXYQUINOLINE;4,8-dimethylquinolin-2(1H)-one
• CAS NO: 5349-78-0
• Molecular Formula: C₁₁H₁₁NO
• Molecular Weight: 173.21
• Mol File: 5349-78-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: 219-221°C
• Boiling Point: 343.3°C at 760 mmHg
• Flash Point: 201.7°C
• Appearance: /
• Density: 1.107g/cm³
• Vapor Pressure: 7.11E-05mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: 4,8-DIMETHYL-2-QUINOLINOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4,8-DIMETHYL-2-QUINOLINOL(5349-78-0)
• EPA Substance Registry System: 4,8-DIMETHYL-2-QUINOLINOL(5349-78-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 5349-78-0(Hazardous Substances Data)

Usage

General Description

4,8-DIMETHYL-2-QUINOLINOL is a chemical compound with the molecular formula C12H11NO. It is a derivative of quinoline and features two methyl groups at the 4 and 8 positions of the quinolinol ring. 4,8-DIMETHYL-2-QUINOLINOL is known for its versatile properties and has been utilized in various industrial and laboratory applications. It has been used as a building block for the synthesis of complex organic molecules, as a ligand in coordination chemistry, and as a catalyst in organic reactions. Additionally, 4,8-DIMETHYL-2-QUINOLINOL has been employed as an additive in commercial products like lubricants and dyes. Its unique structure and properties make it a valuable and versatile chemical compound with a wide range of potential applications.

InChI:InChI=1/C11H11NO/c1-7-4-3-5-9-8(2)6-10(13)12-11(7)9/h3-6H,1-2H3,(H,12,13)

Upstream product

• 93-68-5 3-oxo-N-o-tolylbutanamide 
• 95-53-4 o-toluidine 
• 141-97-9 ethyl acetoacetate 
• 124-38-9 carbon dioxide 
• 107859-36-9 2-methyl-6-(1-methylethenyl)benzenamine 
• 4053-40-1 4-methylquinoline 1-oxide 
• 53848-17-2 2-bromo-6-methylaniline 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 3913-17-5 2-chloro-4,8-dimethyl-quinoline 
• 13362-80-6 4,8-dimethylquinoline 
• 53761-60-7 4,8-dimethyl-2-mercaptoquinoline 
• 370843-65-5 (4,8-dimethyl-[2]quinolylmercapto)-acetic acid 
• 141053-40-9 C₁₉H₁₈N₄O₂S 

Relevant articles and documents

Computational and Synthetic approach with Biological Evaluation of Substituted Quinoline derivatives as small molecule L858R/T790M/C797S triple mutant EGFR inhibitors targeting resistance in Non-Small Cell Lung Cancer (NSCLC)

New substituted quinoline derivatives were designed and synthesized via a five-step modified Suzuki coupling reaction. A comparative molecular docking study was carried out on two different types of EGFR enzymes which include wild-type (PDB: 4I23) and T790M mutated (PDB: 2JIV) respectively. Compounds were also validated upon T790M/C797S mutated (PDB ID: 5D41) EGFR enzyme at the allosteric binding site. All docking studies confirmed high potency and flexibility towards wild type as well as a mutated enzyme. Anticancer activity of the synthesized derivatives was examined against HCC827, H1975 (L858R/T790M/C797S and L858R/T790M), A549, and HT-29 cell lines by standard MTT assay. Most of the quinoline derivatives revealed a significant cytotoxic effect. The IC50 values of 4-(4-methylquinolin-2-yl)phenyl 4-(chloromethyl)benzoate (5j) were found to be 0.0042 μM, 0.02 μM, 1.91 μM, 3.82 μM and 3.67 μM while IC50 values of osimertinib were 0.0040 μM, 0.02 μM, ND, 0.99 μM and 1.22 μM, respectively. Compound 5j has shown excellent inhibitory activities against EGFR kinases triple mutant with IC 50 value 1.91 μM. It was observed that, compared to H1975, A549 and A431 cell lines, synthesized compounds significantly inhibited proliferation of the HCC827 cell line. These data suggested that synthesized compounds showed promising selective anticancer activity against tumor cells harboring EGFR Del E746-A750. The potency of compound 5j was compared through molecular dynamic simulations and an insilico ADMET study. QSAR models were generated and the best model was correctly compared with respect to predicted and observed activity of compounds. The built model will assist to design, refine and construct novel substituted quinoline derivatives as potent EGFR inhibitors in near future.

Lactamization of alkenyl C-H bonds to generate 2-quinolinones with triphosgene

A simple and easy-going method is developed to synthesize the analogues of 2-quinolinones by using triphosgene (BTC) as the carbonyl source. In these reactions, both the toxic carbon monoxide (CO) and phosgene are avoided and the 2-quinolinones are obtained in moderate to good yields under mild conditions, all of which are anticipated to be meaningful in both industry and laboratory.

Synthesis of 2-Quinolinones via a Hypervalent Iodine(III)-Mediated Intramolecular Decarboxylative Heck-Type Reaction at Room Temperature

A hypervalent iodine(III)-mediated intramolecular decarboxylative Heck-type reaction of 2-vinyl-phenyl oxamic acids has been developed. The unique ring-strain-enabled radical decarboxylation mechanism is preliminarily revealed. This protocol features metal-free reaction conditions and operational simplicity, allowing the lactamization of 2-vinylanilines using a readily accessible carbonyl source and the synthesis of various 2-quinolinones with excellent chemoselectivity at room temperature.