103030-28-0

Basic information

• Product Name: 6-BROMO-2-METHYL-4-QUINOLINOL
• Synonyms: 6-BROMO-4-HYDROXY-2-METHYLQUINOLINE;6-BROMO-2-METHYL-4-QUINOLINOL;6-BROMO-2-METHYLQUINOLIN-4-OL;Ux00004208;6-bromo-2-methyl-4-quinolinol(SALTDATA: FREE);2-Methyl-4-hydroxy-6-broMoquinoline
• CAS NO: 103030-28-0
• Molecular Formula: C₁₀H₈BrNO
• Molecular Weight: 238.08
• Mol File: 103030-28-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 338 °C
• Boiling Point: 368.8±37.0 °C at 760 mmHg
• Flash Point: 176.9±26.5 °C
• Appearance: /
• Density: 1.6±0.1 g/cm³
• Vapor Pressure: 0.000192mmHg at 25°C
• Refractive Index: 1.606
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.98±0.40(Predicted)
• CAS DataBase Reference: 6-BROMO-2-METHYL-4-QUINOLINOL(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-2-METHYL-4-QUINOLINOL(103030-28-0)
• EPA Substance Registry System: 6-BROMO-2-METHYL-4-QUINOLINOL(103030-28-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 103030-28-0(Hazardous Substances Data)

Usage

General Description

6-BROMO-2-METHYL-4-QUINOLINOL is a chemical compound with the formula C10H8BrNO. It is a derivative of quinolinol, a class of heterocyclic compounds commonly used as building blocks in the synthesis of pharmaceuticals and agrochemicals. This specific compound is characterized by the presence of a bromine atom at position 6 and a methyl group at position 2 of the quinolinol ring. It is a pale yellow solid that is sparingly soluble in water but more soluble in organic solvents. 6-BROMO-2-METHYL-4-QUINOLINOL has diverse applications in organic synthesis, particularly in the preparation of pharmaceuticals and coordination complexes for catalytic processes. Due to its structural features and reactivity, it has the potential for various pharmacological and chemical research applications.

InChI:InChI=1/C10H8BrNO/c1-6-4-10(13)8-5-7(11)2-3-9(8)12-6/h2-5H,1H3,(H,12,13)

Upstream product

• 37509-21-0 6-bromo-2-methylquinoline-4-carboxylic acid 
• 71940-33-5 3-(4-bromo-anilino)-crotonic acid ethyl ester 
• 106-40-1 4-bromo-aniline 
• 87-48-9 5-Bromo-1H-indole-2,3-dione 
• 141-97-9 ethyl acetoacetate 
• 71940-33-5 ethyl 3-(4-bromophenylamino)but-2-enoate 
• 105-45-3 acetoacetic acid methyl ester 

Downstream Products

• 53364-85-5 6-bromo-4-chloro-2-methylquinoline 
• 96938-26-0 6-bromo-2-methyl-[4]quinolylamine 
• 1070879-53-6 4,6-dibromo-2-methylquinoline 
• 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.

SAR and identification of 2-(quinolin-4-yloxy)acetamides as Mycobacterium tuberculosis cytochrome bc 1 inhibitors

A previous phenotypic screen by GSK identified 2-(quinolin-4-yloxy)acetamides as potent growth inhibitors of Mycobacterium tuberculosis (Mtb). We report the results of a preliminary structure-activity relationship (SAR) study of the compound class which has yielded more potent inhibitors. An Mtb cytochrome bd oxidase deletion mutant (cydKO) was found to be hypersensitive to most members of the compound library, while strains carrying single-nucleotide polymorphisms of the qcrB gene, which encodes a subunit of the menaquinol cytochrome c oxidoreductase (bc1) complex, were resistant to the library. These results identify that the 2-(quinolin-4-yloxy)acetamide class of Mtb growth inhibitors can be added to the growing number of scaffolds that target the M. tuberculosis bc1 complex.

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.