42881-66-3

Basic information

• Product Name: 4-BROMO-6-METHOXYQUINOLINE
• Synonyms: 4-BROMO-6-METHOXYQUINOLINE;4-BROMO-6-METHOXYQUINOLIN
• CAS NO: 42881-66-3
• Molecular Formula: C₁₀H₈BrNO
• Molecular Weight: 238.08
• EINECS: -0
• Product Categories: Quinoline&Isoquinoline
• Mol File: 42881-66-3.mol

Chemical Properties

• Melting Point: 106 °C
• Boiling Point: 336.881 °C at 760 mmHg
• Flash Point: 157.54 °C
• Appearance: /
• Density: 1.517 g/cm³
• Vapor Pressure: 0.000213mmHg at 25°C
• Refractive Index: 1.64
• Storage Temp.: 2-8°C
• PKA: 3.42±0.16(Predicted)
• CAS DataBase Reference: 4-BROMO-6-METHOXYQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-6-METHOXYQUINOLINE(42881-66-3)
• EPA Substance Registry System: 4-BROMO-6-METHOXYQUINOLINE(42881-66-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 42881-66-3(Hazardous Substances Data)

Usage

Chemical Properties

yellow powder

Synthesis Reference(s)

The Journal of Organic Chemistry, 72, p. 2232, 2007 DOI: 10.1021/jo062168u

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

Upstream product

• 13788-72-2 6-methoxy-4(1H)-quinolinone 
• 23432-39-5 4-hydroxy-6-methoxyquinoline 
• 25063-43-8 2,2-dimethyl-5-(((4-methoxyphenyl)amino)methylene)-1,3-dioxane-4,6-dione 
• 104-94-9 4-methoxy-aniline 
• 6279-51-2 6-methoxy-4-aminoquinoline 

Downstream Products

• 522-66-7 dihydroquinine 
• 876492-00-1 4-iodo-6-methoxyquinoline 
• 1229624-37-6 C₂₂H₂₉N₃O₅ 
• 4363-94-4 6-methoxyquinoline-4-carbaldehyde 
• 19834-77-6 methyl 6-methoxyquinoline-4-carboxylate 
• 92288-15-8 (6-methoxyquinolin-4-yl)methanol 
• 51743-68-1 epi-dihydroquinine 
• 1435-55-8 dihydroquinidine 
• 14645-32-0 epi-dihydroquinidine 

Relevant articles and documents

Synthesis and anti-staphylococcal activity of novel bacterial topoisomerase inhibitors with a 5-amino-1,3-dioxane linker moiety

Novel bacterial type II topoisomerase inhibitors (NBTIs) constitute a promising new class of antibacterial agents. We report a series of NBTIs with potent anti-staphylococcal activity and diminished hERG inhibition. Dioxane-linked compound 9 demonstrated MICs ≤1 μg/mL against both methicillin-susceptible (MSSA) and -resistant Staphylococcus aureus (MRSA), accompanied by reduced hERG inhibition as compared to cyclohexane- or piperidine-linked analogs.

TYPE II TOPOISOMERASE INHIBITORS AND METHODS OF MAKING AND USING THEREOF

Disclosed are Type II Topoisomerase Inhibitors, analogs thereof, pharmaceutical compositions thereof, and methods of making and using these compounds and compositions. Methods of using the disclosed compounds to treat infections, such as MRSA, MDR P. aeruginosa, and other pathogens are also described.

Direct access of the chiral quinolinyl core of cinchona alkaloids via a br?nsted acid and chiral amine co-catalyzed chemo- and enantioselective α-alkylation of quinolinylmethanols with enals

A strategy for the facile construction of the chiral quinolinylmethanolic structure, a core featured in cinchona alkaloids, is reported. A new reactivity is harnessed by TfOH-promoted chemoselective activation of α-C-H over O-H bond in quinolinylmethanols. The new reactivity is successfully engineered with an iminium catalysis in a synergistic manner to create a powerful conjugate addition-cyclization cascade process for synthesis of chiral quinoline derived π-butyrolactones in good yields and with good to excellent enantioselectivities. The method enables the first total synthesis of natural product broussonetine in three steps.

The design, synthesis, in silico ADME profiling, antiplasmodial and antimycobacterial evaluation of new arylamino quinoline derivatives

A series of new arylamino quinoline derivatives was designed based on the quinine and mefloquine scaffolds and evaluated in vitro for antiplasmodial and antimycobacterial activities. A number of these compounds exhibited significant activity against the d

Flexible palladium-catalysed amidation reactions for the synthesis of complex aryl amides

This Letter describes the synthesis of complex aryl amides using palladium-catalysed amidation reactions. Use of these conditions allowed for the coupling of a variety of aryl halides and triflates with a host of primary amides in high yields.

From serendipity to rational antituberculosis drug discovery of mefloquine-isoxazole carboxylic acid esters

Both in vitro and in vivo metabolism studies suggested that 5-(2,8-bis(trifluoromethyl)quinolin-4-yloxymethyl)isoxazole-3-carboxylic acid ethyl ester (compound 3) with previously reported antituberculosis activity is rapidly converted to two metabolites 3

Novel pyrazole derivatives as potent inhibitors of type II topoisomerases. Part 1: Synthesis and preliminary SAR analysis

In an attempt to search for a new class of antibacterial agents, we have discovered a series of pyrazole analogs that possess good antibacterial activity for Gram-positive and Gram-negative organisms via inhibition of type II bacterial topoisomerases. We have investigated the structure-activity relationships of this series, with an emphasis on the length and conformation of the linker. This work led to the identification of tetrahydroindazole analogs, such as compound 1, as the most potent class of compounds.

ANTIBACTERIAL AGENTS

Naphthalene, quinoline, quinoxaline and naphthyridine derivatives useful in the treatment of bacterial infections in mammals, particularly humans, are disclosed herein.

Bicyclic pyrazole compounds as antibacterial agents

Antibacterial compounds, compositions containing them, and methods of use for the inhibition of bacterial activity and the treatment, prevention or inhibition of bacterial infection.

ANTIBACTERIAL AGENTS

Naphthalene, quinoline, quinoxaline and naphthyridine derivatives useful in the treatment of bacterial infections in mammals, particularly humans, are disclosed herein.