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

Description

4-CHLORO-2,6-DIMETHYLQUINOLINE is a quinoline derivative with the molecular formula C11H10ClN, featuring a chlorine atom and two methyl groups on the quinoline ring. This chemical compound serves as a versatile building block in the synthesis of pharmaceuticals and agrochemicals, and it also exhibits antimicrobial and antifungal properties, positioning it as a promising candidate for new drug development. Furthermore, its potential applications extend to organic light-emitting diodes (OLEDs) and other areas within the optical and electronic industries.

Uses

Used in Pharmaceutical and Agrochemical Industries:
4-CHLORO-2,6-DIMETHYLQUINOLINE is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure allows for the development of compounds with specific therapeutic or pesticidal properties, contributing to the advancement of medicine and agriculture.
Used in Antimicrobial and Antifungal Applications:
Due to its antimicrobial and antifungal properties, 4-CHLORO-2,6-DIMETHYLQUINOLINE is utilized as an active ingredient in the development of new drugs targeting a range of microbial infections, offering potential solutions to the growing issue of antibiotic resistance.
Used in Organic Light-Emitting Diodes (OLEDs) Industry:
4-CHLORO-2,6-DIMETHYLQUINOLINE is employed in the research and development of organic light-emitting diodes (OLEDs). Its electronic properties make it a candidate for improving the performance and efficiency of OLEDs, which are used in various display and lighting applications.
Used in Optical and Electronic Applications:
Beyond OLEDs, 4-CHLORO-2,6-DIMETHYLQUINOLINE has potential uses in other optical and electronic applications, where its chemical and physical properties can be harnessed to enhance device performance or create innovative technologies.

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

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

Downstream Products

• 109980-01-0 N'-(2,6-dimethyl-[4]quinolyl)-N,N-dimethyl-p-phenylenediamine 
• 877-43-0 2,6-dimethylquinoline 
• 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 

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.