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

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

Uses

Used in Pharmaceutical Synthesis:
6-BROMO-2-METHYL-4-QUINOLINOL is used as a key intermediate in the synthesis of various pharmaceuticals due to its unique structural features and reactivity. Its presence in the molecular structure can contribute to the development of new drugs with improved therapeutic properties.
Used in Agrochemical Production:
6-BROMO-2-METHYL-4-QUINOLINOL is also utilized in the production of agrochemicals, where its chemical properties can enhance the effectiveness of pesticides, herbicides, and other agricultural chemicals, leading to better crop protection and yield.
Used in Organic Synthesis:
6-BROMO-2-METHYL-4-QUINOLINOL serves as a versatile building block in organic synthesis, allowing for the creation of a wide range of organic compounds with diverse applications in various industries.
Used in Coordination Complexes for Catalysis:
6-BROMO-2-METHYL-4-QUINOLINOL is employed in the formation of coordination complexes, which are used as catalysts in various chemical processes. Its unique structure and reactivity contribute to the efficiency and selectivity of these catalytic systems.
Used in Chemical Research:
6-BROMO-2-METHYL-4-QUINOLINOL is utilized in chemical research for studying reaction mechanisms, exploring new synthetic routes, and developing innovative applications in the field of chemistry.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 6-BROMO-2-METHYL-4-QUINOLINOL is used for the design and synthesis of novel bioactive molecules, potentially leading to the discovery of new therapeutic agents with improved pharmacological properties.

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.

New insights into the SAR and drug combination synergy of 2-(quinolin-4-yloxy)acetamides against Mycobacterium tuberculosis

2-(Quinolin-4-yloxy)acetamides have been described as potent and selective in vitro inhibitors of Mycobacterium tuberculosis (Mtb) growth. Herein, a new series of optimized compounds were found to demonstrate highly potent antitubercular activity, with minimum inhibitory concentration (MIC) values against drug-susceptible and drug-resistant Mycobacterium tuberculosis strains in the submicromolar range. Furthermore, the most active compounds had no apparent toxicity to mammalian cells, and they showed intracellular activities similar to those of isoniazid and rifampin in a macrophage model of Mtb infection. Use of the checkerboard method to investigate the association profiles of lead compounds with first- and second-line antituberculosis drugs showed that 2-(quinolin-4-yloxy)acetamides have a synergistic effect with rifampin. Ultimately, the good permeability, moderate rates of metabolism and low risk of drug-drug interactions displayed by some of the synthesized compounds indicate that 2-(quinolin-4-yloxy)acetamides may yield candidates to use in the development of novel alternative therapeutics for tuberculosis treatment.

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.

QUINOLINE-BASED KINASE INHIBITORS

The present disclosure is generally directed to compounds of formula (I) which can inhibit AAKI (adaptor associated kinase 1), compositions comprising such compounds, and methods for inhibiting AAKI.

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.

Novel quinoline and naphthalene derivatives as potent antimycobacterial agents

We have designed and synthesized both the quinoline and naphthalene based molecules influenced by the unique structural make-up of mefloquine and TMC207, respectively. These compounds were evaluated for their anti-mycobacterial activity against drug sensi

COMPOSITIONS AND METHODS FOR MODULATING GATED ION CHANNELS

Disclosed are quinoline and quinazoline compounds which modulate the activity of the gated ion channels. Compounds that modulate these gated ion channels are useful in the treatment of diseases and disorders related to pain, inflammation, the neurological system, the gastrointestinal system and genitourinary system. Preferred compounds include quinoline or quinazoline derivatives substituted at the 4- position via N(H), C(O) or O moieties.