53364-85-5

Basic information

• Product Name: 6-BROMO-4-CHLORO-2-METHYLQUINOLINE
• Synonyms: 6-BROMO-4-CHLOROQUINALDINE;6-BROMO-4-CHLORO-2-METHYLQUINOLINE
• CAS NO: 53364-85-5
• Molecular Formula: C₁₀H₇BrClN
• Molecular Weight: 256.53
• Mol File: 53364-85-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 75 °C
• Boiling Point: 321.9 °C at 760 mmHg
• Flash Point: 148.5 °C
• Appearance: /
• Density: 1.591 g/cm³
• Vapor Pressure: 0.000546mmHg at 25°C
• Refractive Index: 1.661
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 3.57±0.50(Predicted)
• CAS DataBase Reference: 6-BROMO-4-CHLORO-2-METHYLQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-4-CHLORO-2-METHYLQUINOLINE(53364-85-5)
• EPA Substance Registry System: 6-BROMO-4-CHLORO-2-METHYLQUINOLINE(53364-85-5)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25-41
• Safety Statements: 26-39-45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 53364-85-5(Hazardous Substances Data)

Usage

General Description

6-Bromo-4-Chloro-2-Methylquinoline is a synthetic organic compound which is incorporated in many industrial applications due to its chemical properties. It is structured as an aromatic heterocyclic piece, marked with the presence of nitrogen atom, amongst others. Notably, it's an organobromine compound which is an integral member of quinolines: a class of compounds known for their wide use in pharmaceuticals and dyestuffs. As with chemicals similar in nature, proper handling and storage is necessary to ensure safety and to prevent any harmful reactions as it may have hazardous properties. Currently, it is primarily utilized for research and development within laboratories and chemical plants.

InChI:InChI=1/C10H7BrClN/c1-6-4-9(12)8-5-7(11)2-3-10(8)13-6/h2-5H,1H3

Upstream product

• 112182-47-5 6-bromo-4-hydroxy-2-methylquinoline 
• 106-40-1 4-bromo-aniline 
• 71940-33-5 3-(4-bromo-anilino)-crotonic acid ethyl ester 
• 103030-28-0 6-bromo-4-hydroxy-2-methylquinoline 
• 71940-33-5 ethyl 3-(4-bromophenylamino)but-2-enoate 

Downstream Products

• 1126485-28-6 4-[(2-aminophenyl)thio]-6-bromo-2-methylquinoline hydrochloride 
• 951625-89-1 C₁₀H₁₀BrN₃ 

Relevant articles and documents

Anticancer, antimicrobial activities of quinoline based hydrazone analogues: Synthesis, characterization and molecular docking

Based on the biologically active heterocycle quinoline, a series (18a-p) of quinoline hydrazone analogues were prepared, starting from 6-bromo/6-chloro-2-methyl-quinolin-4-yl-hydrazines. For all the newly synthesized compounds cytotoxic activities were carried out at the National Cancer Institute (NCI), USA, against full NCI 60 human cancer cell lines. Amongst all the tested compounds, nine compounds (18b, 18d, 18e, 18f, 18g, 18h, 18i, 18j, 18l) exhibited important anti-proliferative activity at 10 μM concentration and were further screened at 10-fold dilutions of five different concentrations (0.01, 0.1, 1, 10 and 100 μM) with GI50 values ranging from 0.33 to 4.87 μM and LC50 values ranging from 4.67 μM to >100j μM. Further, the mean values of GI50, TGI and LC50 of the most potent compound 18j were compared with the clinically used anticancer agents bendamustine and chlorambucil, revealed that the quinolyl hydrazones holds promise as a potential anticancer agents. Further all the newly prepared compounds were screened for their antimicrobial activity. All the quinolyl hydrazones displayed good to excellent antimicrobial activity with MIC values ranging from 6.25 to 100 μg/mL against the tested pathogenic strains. Molecular docking of the synthesized compounds into the active binding site of human DNA topoisomerase I (htopoI) was carried out to predict the binding mode to the DNA topoisomerase I inhibitors. Hopefully in future, compounds based on quinoline core could be used as a lead compounds for designing new anticancer agents.

Myobacterium Tuberculosis-Thioredoxin Reductase Inhibitor as an Antitubercular Agent

The invention relates to Mycobacterium tuberculosis-thioredoxin reductase inhibitors, processes for the preparation thereof, drugs containing said compounds, and the use of said compounds for manufacturing drugs.

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.