6270-08-2

Basic information

• Product Name: 4-CHLORO-2,6-DIMETHYLQUINOLINE
• Synonyms: 4-CHLORO-6-METHYLQUINALDINE;4-CHLORO-2,6-DIMETHYLQUINOLINE;4-Chloro-2,6-dimethylquinoline AldrichCPR
• CAS NO: 6270-08-2
• Molecular Formula: C₁₁H₁₀ClN
• Molecular Weight: 191.66
• Mol File: 6270-08-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 285.9°C at 760 mmHg
• Flash Point: 154°C
• Appearance: /
• Density: 1.188g/cm³
• Vapor Pressure: 0.00471mmHg at 25°C
• Refractive Index: 1.621
• CAS DataBase Reference: 4-CHLORO-2,6-DIMETHYLQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-2,6-DIMETHYLQUINOLINE(6270-08-2)
• EPA Substance Registry System: 4-CHLORO-2,6-DIMETHYLQUINOLINE(6270-08-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 6270-08-2(Hazardous Substances Data)

Usage

General Description

4-CHLORO-2,6-DIMETHYLQUINOLINE is a chemical compound with the molecular formula C11H10ClN. It is a quinoline derivative that contains a chlorine atom and two methyl groups on the quinoline ring. 4-CHLORO-2,6-DIMETHYLQUINOLINE is often used as a building block in the synthesis of various pharmaceuticals and agrochemicals. It has also been found to exhibit antimicrobial and antifungal properties, making it a potential candidate for the development of new drugs. Additionally, 4-CHLORO-2,6-DIMETHYLQUINOLINE has been studied for its potential use in organic light-emitting diodes (OLEDs) and other optical and electronic applications. However, it is important to note that this compound may have various safety and health hazards, and should be handled with proper care and precautions.

InChI:InChI=1/C11H10ClN/c1-7-3-4-11-9(5-7)10(12)6-8(2)13-11/h3-6H,1-2H3

Upstream product

• 33240-21-0 ethyl 3-(p-tolylamino)but-2-enoate 
• 106-49-0 p-toluidine 
• 103-89-9 4-Methylacetanilide 
• 25428-07-3 4-hydroxy-2,6-dimethylquinoline 
• 15644-82-3 2,6-dimethyl-quinolin-4-ol 

Downstream Products

• 87602-53-7 1-(2,6-Dimethyl-quinolin-4-yl)-4-phenyl-piperidin-4-ol 
• 79340-66-2 4-(2,6-Dimethyl-quinolin-4-ylamino)-2-hydroxy-benzoic acid ethyl ester; hydrochloride 
• 87602-52-6 {4-[4-(2-Chloro-phenyl)-piperazin-1-yl]-phenyl}-(2,6-dimethyl-quinolin-4-yl)-amine 
• 79340-83-3 4-(2,6-Dimethyl-quinolin-4-ylamino)-benzoic acid ethyl ester; hydrochloride 
• 1126485-20-8 4-[(2-aminophenyl)thio]-2,6-dimethylquinoline hydrochloride 
• 29125-48-2 4-hydrazino-2,6-dimethylquinoline 
• 1373399-60-0 C₂₈H₂₀N₂ 

Relevant articles and documents

Green and Efficient Synthesis of 4-Heteryl-Quinolines and Their Antibacterial Evaluations

A green and efficient synthesis of 4-heteryl-quinolines (9a, 9b, 9c, 9d), (10a, 10b, 10c, 10d) and (11a, 11b, 11c, 11d) has been described using PEG-600 as a green solvent. Initially, 4-chloro-2-methylquinolines (5a, 5b, 5c, 5d) on reaction with aromatic heterocyclic thiols (6), (7), and (8) using PEG-600 at 100°C for 30–40 min resulted in (9), (10), and (11) in good yields. Alternatively, (9), (10), and (11) could also be prepared in dimethylformamide using K2CO3 as base and tetrabutylammonium bromide as phase transfer catalyst at 100°C for 1–2 h. All the compounds were synthesized and characterized by IR, NMR, mass spectroscopy, and 13C NMR analysis. All synthesized compounds were screened for their antibacterial activity against clinical strains that include Gram-positive (Bacillus subtilis MTCC 121, staphylococcus aureus MLS-16 MTCC 2940, Micrococcus lutes MTCC 2470, and Staphylococcus aureus MTCC 96) and Gram-negative bacteria (Candida albicans MTCC 3017, Klebsiella planticola MTCC 530, Escherichia coli MTCC 739, and Pseudomonas aeruginosa MTCC 2453). The results revealed that compounds (9a, 9d, 10a, 10c, 11b, and 11d) exhibited significant antibacterial activity almost equal to the standard drug, that is, Ciprofloxacin.

Synthesis of 6-methylbenzo-[b]pyrido[3,2-f][1,6]naphthyridines from 4-chloro-2-methylquinoline

4-Chloro-2-methylquinolines in reaction with 3-aminopyridine yielded 4-quinolinamines, which upon cyclisation under Vilsmeier-Haak conditions afforded the title compounds. 2005 Springer Science+Business Media, Inc.

Quinoline derivatives as antitubercular/antibacterial agents

A number of quinoline derivatives of known antibacterial agents have been prepared and tested against the micro-organisms S. coli, S. paratyphi B, S. aureus and in particular against Mycobacterium tuberculosis H37-Rv. It has not been possibfe to establish correlation between antibacterial and antitubercular activities of these compounds. However, the antitubercular effect at MIC of 5 μg/mL against H37Rv shows that many modified compounds are more inhibitory than the parent agents such as 3-aminophenol, sulphamethoxazole, sulphaphenazole, sulphathiazole and monoacetyldapsone; among these the most effective are those with substituents such as 6-methyl, 6-chloro, 6-ethoxy-, or 8-methoxy functions in quinoline moiety.