13235-12-6

Basic information

• Product Name: 4-bromo-2-methylquinolin-3-ol
• Synonyms: 4-bromo-2-methylquinolin-3-ol;4-Bromo-2-methyl-3-quinolinol;Einecs 236-208-5
• CAS NO: 13235-12-6
• Molecular Formula: C₁₀H₈BrNO
• Molecular Weight: 238.08062
• EINECS: 236-208-5
• Mol File: 13235-12-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 164～166℃
• Boiling Point: 323.3°C at 760 mmHg
• Flash Point: 149.3°C
• Appearance: /
• Density: 1.612g/cm³
• Vapor Pressure: 0.00014mmHg at 25°C
• Refractive Index: 1.692
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-bromo-2-methylquinolin-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromo-2-methylquinolin-3-ol(13235-12-6)
• EPA Substance Registry System: 4-bromo-2-methylquinolin-3-ol(13235-12-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 13235-12-6(Hazardous Substances Data)

Usage

General Description

4-bromo-2-methylquinolin-3-ol is a chemical compound with the molecular formula C10H8BrNO, which belongs in the quinoline family. It is a derivative of quinolin-3-ol, with a bromine atom attached at the 4th position and a methyl group at the 2nd position. 4-bromo-2-methylquinolin-3-ol has diverse applications in the field of organic synthesis and pharmaceuticals. It is often used as a building block in the production of various pharmaceutical and agrochemical products. Additionally, 4-bromo-2-methylquinolin-3-ol has been studied for its potential biological activities, including its antimicrobial and antitumor properties, making it a valuable compound in both research and industrial settings.

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

Upstream product

• 117-57-7 3-hydroxy-2-methyl-4-quinolinecarboxylic acid 
• 552-89-6 2-nitro-benzaldehyde 
• 613-19-4 3-hydroxy-quinaldine 
• 50488-44-3 4-Bromo-2-methylquinoline 

Downstream Products

• 1345515-22-1 2-methyl-3-hydroxy-4-acetylquinoline 
• 34497-54-6 3-hydroxy-2-methyl-quinolin-4(1H)-one 

Relevant articles and documents

Discovery of MK-8831, A Novel Spiro-Proline Macrocycle as a Pan-Genotypic HCV-NS3/4a Protease Inhibitor

We have been focused on identifying a structurally different next generation inhibitor to MK-5172 (our Ns3/4a protease inhibitor currently under regulatory review), which would achieve superior pangenotypic activity with acceptable safety and pharmacokinetic profile. These efforts have led to the discovery of a novel class of HCV NS3/4a protease inhibitors containing a unique spirocyclic-proline structural motif. The design strategy involved a molecular-modeling based approach, and the optimization efforts on the series to obtain pan-genotypic coverage with good exposures on oral dosing. One of the key elements in this effort was the spirocyclization of the P2 quinoline group, which rigidified and constrained the binding conformation to provide a novel core. A second focus of the team was also to improve the activity against genotype 3a and the key mutant variants of genotype 1b. The rational application of structural chemistry with molecular modeling guided the design and optimization of the structure-activity relationships have resulted in the identification of the clinical candidate MK-8831 with excellent pan-genotypic activity and safety profile.

Simple synthesis of 3-hydroxyquinolines via Na2S2O4-mediated reductive cyclization of (2-(2-nitrophenyl)oxiran-1-yl)(aryl)methanones (o-nitrobenzalacetophenone oxides)

An efficient sodium dithionite (Na2S2O4)-mediated method for construction of 3-hydroxyquinolines via in situ Meinwald rearrangement/intramolecular reductive cyclization of o-nitrobenzalacetophenone oxides has been developed. The practical approach is of excellent functional group compatibility with as high as 98% yield under mild reaction conditions. Moreover, further manipulation successfully furnished 4-bromo substituted derivatives which may provide a promising potential application in exploring biologically active analogs of 3-hydroxyquinolines.