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

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

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 
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• 33240-21-0 ethyl 3-(p-tolylamino)but-2-enoate 
• 25428-07-3 4-hydroxy-2,6-dimethylquinoline 

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 
• 123636-66-8 N-[4-[N-(4-chloro-2-methylquinolin-6-ylmethyl)-N-(prop-2-ynyl)amino]-2-fluorobenzoyl]-L-glutamic acid 
• 141848-56-8 (S)-2-{4-[(4-Chloro-2-methyl-quinolin-6-ylmethyl)-amino]-benzoylamino}-pentanedioic acid 
• 123636-91-9 (S)-2-{4-[(4-Chloro-2-methyl-quinolin-6-ylmethyl)-methyl-amino]-benzoylamino}-pentanedioic acid 
• 123636-90-8 (S)-2-{4-[(4-Chloro-2-methyl-quinolin-6-ylmethyl)-ethyl-amino]-benzoylamino}-pentanedioic acid 
• 123637-06-9 (S)-2-{4-[(4-Chloro-2-hydroxymethyl-quinolin-6-ylmethyl)-ethyl-amino]-benzoylamino}-pentanedioic acid 

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.

N1-{4-[(10S)-Dihydroartemisinin-10-oxyl]}phenylmethylene-N 2-(2-methylquinoline-4-yl)hydrazine derivatives as antiplasmodial falcipain-2 inhibitors

A series of N1-{4-[(10S)-dihydroartemisinin- 10-oxyl]}phenylmethylene-N2-(2-methylquinoline-4-yl) hydrazine derivatives 9a-9n possessing 4-quinolylhydrazone and artemisinin cores were herein synthesized and evaluated for their activities against cysteine protease falcipain- 2 of Plasmodium falciparum. The structures were clearly confirmed by elemental analysis, 1H NMR, and mass spectra. The pharmacological results indicated that all compounds showed excellent activity against recombinant falcipain-2 (IC50 = 0.15-2.28 μM). The best one of this series was compound 9d (IC50 = 0.15 μM). The molecular docking results showed that the compound 9d made close contact with the key active site of cysteine protease falcipain-2.

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.

Aminoquinoline compounds

This invention relates to treating inflammatory and immune diseases with certain aminoquinoline compounds that bind to CXCR3 receptors. The aminoquinoline compounds are covered by the formula (I) shown below. Each variable is defined in the specification.

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.

Quinoline derivatives having anti-tumor activity

The invention relates to a quinoline of the formula: STR1 wherein each of R1 and R2, which may be the same or different, is hydrogen, halogeno, hydroxy, cyano, carbamoyl, nitro or amino, alkyl, alkoxy, alkylthio, alkylamino, dialkyla

Quinoline antifolate thymidylate synthase inhibitors: Variation of the C2- and C4-substituents

Modifications to the bicyclic ring system of the potent thymidylate synthase (TS) inhibitor N-[4-[N-[(2-amino-3,4-dihydro-4-oxo-6- quinazolinyl)methyl]-N-prop-2-ynylamino]benzoyl]-L-glutamic acid (1, CB3717) have led to the synthesis of a series of quinol