172939-50-3

Basic information

• Product Name: 8-bromo-4-methylquinoline
• Synonyms: 8-bromo-4-methylquinoline;Quinoline, 8-broMo-4-Methyl-;8-Bromo-4-methylquinolin
• CAS NO: 172939-50-3
• Molecular Formula: C10H8BrN
• Molecular Weight: 222.084
• Mol File: 172939-50-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 315.773 °C at 760 mmHg
• Flash Point: 144.774 °C
• Appearance: /
• Density: 1.488 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.654
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 8-bromo-4-methylquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 8-bromo-4-methylquinoline(172939-50-3)
• EPA Substance Registry System: 8-bromo-4-methylquinoline(172939-50-3)

Safety Data

• Hazardous Substances Data: 172939-50-3(Hazardous Substances Data)

Usage

General Description

8-bromo-4-methylquinoline is an organic compound with the molecular formula C10H8BrN. It is a derivative of quinoline and is commonly used as a building block in organic synthesis. This chemical compound is a yellow crystalline solid with a melting point of 80-82°C and a boiling point of 280-300°C. It is insoluble in water but soluble in organic solvents such as ethanol and ether. 8-bromo-4-methylquinoline is commonly used in pharmaceutical and agrochemical industries as an intermediate in the synthesis of various biologically active compounds. Its versatile reactivity and widespread use in organic synthesis make it a valuable chemical compound in scientific research and industrial applications.

InChI:InChI=1/C10H8BrN/c1-7-5-6-12-10-8(7)3-2-4-9(10)11/h2-6H,1H3

Upstream product

• 62748-01-0 4-methyl-8-aminoquinoline 
• 78-94-4 methyl vinyl ketone 
• 615-36-1 2-bromoaniline 

Relevant articles and documents

Synthesis and antileishmanial evaluation of thiazole orange analogs

Cyanine compounds have previously shown excellent in vitro and promising in vivo antileishmanial efficacy, but the potential toxicity of these agents is a concern. A series of 22 analogs of thiazole orange ((Z)-1-methyl-4-((3-methylbenzo[d]thiazol-2(3H)-ylidene)methyl)quinolin-1-ium salt), a commercial cyanine dye with antileishmanial activity, were synthesized in an effort to increase the selectivity of such compounds while maintaining efficacy. Cyanines possessing substitutions on the quinolinium ring system displayed potency against Leishmania donovani axenic amastigotes that differed little from the parent compound (IC50 12–42 nM), while ring disjunction analogs were both less potent and less toxic. Changes in DNA melting temperature were modest when synthetic oligonucleotides were incubated with selected analogs (ΔTm ≤ 5 °C), with ring disjunction analogs showing the least effect on this parameter. Despite the high antileishmanial potency of the target compounds, their toxicity and relatively flat SAR suggests that further information regarding the target(s) of these molecules is needed to aid their development as antileishmanials.

DNA-PK INHIBITORS

The present invention relates to compounds useful as inhibitors of DNA-PK. The invention also provides pharmaceutically acceptable compositions comprising said compounds and methods of using the compositions in the treatment of various disease, conditions, or disorders.

The synthesis and biological evaluation of quinolyl-piperazinyl piperidines as potent serotonin 5-HT1A antagonists

As part of an effort to identify 5-HT1A antagonists that did not possess typical arylalkylamine or keto/amido-alkyl aryl piperazine scaffolds, prototype compound 10a was identified from earlier work in a combined 5-HT 1A antagonist/SSRI program. This quinolyl-piperazinyl piperidine analogue displayed potent, selective 5-HT1A antagonism but suffered from poor oxidative metabolic stability, resulting in low exposure following oral administration. SAR studies, driven primarily by in vitro liver microsomal stability assessment, identified compound 10b, which displayed improved oral bioavailability and lower intrinsic clearance. Further changes to the scaffold (e.g., 10r) resulted in a loss in potency. Compound 10b displayed cognitive enhancing effects in a number of animal models of learning and memory, enhanced the antidepressant-like effects of the SSRI fluoxetine, and reversed the sexual dysfunction induced by chronic fluoxetine treatment.