332366-57-1

Basic information

• Product Name: 6-Bromoquinolin-4(1H)-one
• Synonyms: 6-Bromoquinolin-4(1H)-one;6-BroMo-1H-quinolin-4-one;6-BROMO-1,4-DIHYDROQUINOLIN-4-ONE;6-Bromoquinolin-4(1H);6-Bromo-4(1H)-quinolinone
• CAS NO: 332366-57-1
• Molecular Formula: C₉H₆BrNO
• Molecular Weight: 224.05404
• Mol File: 332366-57-1.mol

Chemical Properties

• Melting Point: 282-284 °C
• Boiling Point: 321.7±42.0 °C(Predicted)
• Appearance: /
• Density: 1.620±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 1.39±0.50(Predicted)
• CAS DataBase Reference: 6-Bromoquinolin-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromoquinolin-4(1H)-one(332366-57-1)
• EPA Substance Registry System: 6-Bromoquinolin-4(1H)-one(332366-57-1)

Safety Data

• Hazardous Substances Data: 332366-57-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Bromoquinolin-4(1H)-one is used as a reagent for the enantioselective preparation of tetrahydroquinolinones and dihydroand tetrahydropyridinones. This is achieved through the copper-catalyzed addition of Grignard reagents to quinolinones and pyridones, which is a crucial step in the synthesis of various biologically active compounds with potential applications in medicine.
Used in Agrochemical Industry:
6-Bromoquinolin-4(1H)-one is also utilized in the development of agrochemicals, specifically as a building block for the synthesis of novel pesticides and herbicides. Its unique structure and reactivity make it a valuable component in the design and synthesis of new molecules with improved efficacy and selectivity in controlling pests and weeds.

Upstream product

• 141-82-2 malonic acid 
• 122-51-0 orthoformic acid triethyl ester 
• 106-40-1 4-bromo-aniline 
• 2033-24-1 cycl-isopropylidene malonate 
• 98948-95-9 6-bromo-4-hydroxyquinoline-3-carboxylic acid 
• 101937-44-4 diethyl 2-((4-bromophenylamino)methylene)malonate 
• 98948-95-9 6-bromo-1,4-dihydro-4-oxo-3-quinoline carboxylic acid 
• 79607-23-1 ethyl 6-bromo-4-oxo-1,4-dihydro-quinoline-3-carboxylate 
• 19056-84-9 diethyl 2-[(p-tolylamino)methylidene]malonate 
• 1320361-74-7 ethyl 3-(4-bromoanilino)propenoate 
• 15568-85-1 5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 187278-01-9 5-(((4-bromophenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 1320361-51-0 6-bromo-1-methyl-3-phenylquinolin-4(1H)-one 
• 1320361-52-1 6-bromo-1-methyl-3-(4-methylphenyl)quinolin-4(1H)-one 
• 1320361-56-5 6-bromo-3-[(E)-2-(4-methoxyphenyl)ethen-1-yl]-1-methylquinolin-4(1H)-one 
• 857762-32-4 6-bromo-3-chloroquinolin-4-ol 

Relevant articles and documents

Cu(I)-Catalyzed Alkynylation of Quinolones

Herein we report the first alkynylation of quinolones with terminal alkynes under mild reaction conditions. The reaction is catalyzed by Cu(I) salts in the presence of a Lewis acid, which is essential for the reactivity of the system. The enantioselective version of this transformation has also been explored, and the methodology has been applied in the synthesis of the enantioenriched tetrahydroquinoline alkaloid cuspareine.

Highly Enantioselective Catalytic Addition of Grignard Reagents to N-Heterocyclic Acceptors

General methods to prepare chiral N-heterocyclic molecular scaffolds are greatly sought after because of their significance in medicinal chemistry. Described here is the first general catalytic methodology to access a wide variety of chiral 2- and 4-substituted tetrahydro-quinolones, dihydro-4-pyridones, and piperidones with excellent yields and enantioselectivities, utilizing a single catalyst system.

6-bromo-4-chloroquinoline preparation method

The invention discloses a 6-bromo-4-chloroquinoline preparation method. 4-bromaniline, ethyl propiolate, phosphorus trichloride and the like are used as raw materials to obtain a target product 6-bromo-4-chloroquinoline through three-step reaction. The 6-bromo-4-chloroquinoline preparation method is convenient and simple in operation and environment friendly, the comprehensive yield is 70% or above and remarkably increased as compared with existing yield which is 26-42%, existing medicine production cost is sharply reduced, and the 6-bromo-4-chloroquinoline preparation method is suitable for industrial mass production.

Synthesis of Fused Pyrimidinone and Quinolone Derivatives in an Automated High-Temperature and High-Pressure Flow Reactor

Fused pyrimidinone and quinolone derivatives that are of potential interest to pharmaceutical research were synthesized within minutes in up to 96% yield in an automated Phoenix high-temperature and high-pressure continuous flow reactor. Heterocyclic scaffolds that are either hard to synthesize or require multisteps are readily accessible using a common set of reaction conditions. The use of low-boiling solvents along with the high conversions of these reactions allowed for facile workup and isolation. The methods reported herein are highly amenable for fast and efficient heterocycle synthesis as well as compound scale-ups.

Antiparasitic Lead Discovery: Toward Optimization of a Chemotype with Activity Against Multiple Protozoan Parasites

Human African trypanosomiasis (HAT), Chagas disease, and leishmaniasis present a significant burden across the developing world. Existing therapeutics for these protozoal neglected tropical diseases suffer from severe side effects and toxicity. Previously

Condensed derivatives of imidazole useful as pharmaceuticals

The invention relates to the compounds (I) and their acids and bases salts: wherein: the dotted line indicates a double bond; X is N or C-R1 and Y is N or C-R2, X and Y not being simultaneously N; A is selected from the group consisting of phenyl, naphthyl and (5-11) membered monocyclic or bicyclic unsaturated cycle or heterocycle possibly substituted as defined in the application, and A can also comprise either a further (4-7) membered heterocycle, said heterocycle being a monocycle, fused, saturated or unsaturated, the polycyclic system then comprising up to 14 members and up to 5 heteroatoms selected from N, O and S; B is Hydrogen or a substituent as defined in the application, or B is a (4-10) membered mono or bicyclic saturated or unsaturated heterocycle containing 1-3 heteroatoms selected from N, O and S, and possibly substituted as defined in the application; B not being Hydrogen when X is N and Y is C-R2; R1 is Hydrogen or a substituent as defined in the application; B and R1 cannot be simultaneously Hydrogen; R2 is Hydrogen or Halogen; their preparation, their use in the antibacterial prevention and therapy, alone or in association with antibacterials, antivirulence agents or drugs reinforcing the host innate immunity, and pharmaceutical compositions and associations containing them.

Protozoan Parasite Growth Inhibitors Discovered by Cross-Screening Yield Potent Scaffolds for Lead Discovery

Tropical protozoal infections are a significant cause of morbidity and mortality worldwide; four in particular (human African trypanosomiasis (HAT), Chagas disease, cutaneous leishmaniasis, and malaria) have an estimated combined burden of over 87 million disability-adjusted life years. New drugs are needed for each of these diseases. Building on the previous identification of NEU-617 (1) as a potent and nontoxic inhibitor of proliferation for the HAT pathogen (Trypanosoma brucei), we have now tested this class of analogs against other protozoal species: T. cruzi (Chagas disease), Leishmania major (cutaneous leishmaniasis), and Plasmodium falciparum (malaria). Based on hits identified in this screening campaign, we describe the preparation of several replacements for the quinazoline scaffold and report these inhibitors' biological activities against these parasites. In doing this, we have identified several potent proliferation inhibitors for each pathogen, such as 4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-6-(4-((4-methyl-1,4-diazepan-1-yl)sulfonyl)phenyl)quinoline-3-carbonitrile (NEU-924, 83) for T. cruzi and N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-7-(4-((4-methyl-1,4-diazepan-1-yl)sulfonyl)phenyl)cinnolin-4-amine (NEU-1017, 68) for L. major and P. falciparum.

[11C]GSK2126458 and [18F]GSK2126458, the first radiosynthesis of new potential PET agents for imaging of PI3K and mTOR in cancers

GSK2126458 is a highly potent inhibitor of phosphoinositide 3-kinase (PI3K) and mammalian target of rapamycin (mTOR) with low picomolar to subnanomolar activity. [11C]GSK2126458 and [18F]GSK212 6458, new potential PET agents for imaging of PI3K and mTOR in cancer, were first designed and synthesized in 40-50% and 20-30% decay corrected radiochemical yield, and 370-740 and 37-222 GBq/lmol specific activity at end of bombardment (EOB), respectively.

Regioselective functionalization of quinolin-4(1H)-ones via sequential palladium-catalyzed reactions

A practical and general synthesis of 1,3,6-trisubstituted quinolin-4(1H)-ones starting from 1-alkyl-6-bromo-3-iodoquinolin-4(1H)-one is described, based on regioselective sequential palladium-catalyzed cross-coupling reactions, namely Suzuki-Miyaura, Sono

Direct C-3-alkenylation of quinolones via palladium-catalyzed C-H functionalization

An unprecedented C-3-alkenylation of quinolones was reported through palladium-catalyzed C-H functionalization with 1% catalyst loading. This method provides an efficient route to a variety of new quinolone derivatives.