53472-18-7

Basic information

• Product Name: 5-BROMO-QUINOLIN-8-YLAMINE
• Synonyms: ART-CHEM-BB B015996;AKOS B015996;AKOS MSC-0726;5-BROMOQUINOLIN-8-AMINE;5-BROMO-QUINOLIN-8-YLAMINE;5-BROMO-8-AMINOQUINOLINE;5-BROMO-8-QUINOLINAMINE;TIMTEC-BB SBB001595
• CAS NO: 53472-18-7
• Molecular Formula: C₉H₇BrN₂
• Molecular Weight: 223.07
• Product Categories: Quinoline&Isoquinoline
• Mol File: 53472-18-7.mol

Chemical Properties

• Melting Point: 109-110 °C
• Boiling Point: 353.3°Cat760mmHg
• Flash Point: 167.5°C
• Appearance: /
• Density: 1.649g/cm³
• Vapor Pressure: 3.61E-05mmHg at 25°C
• Refractive Index: 1.732
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 3.02±0.12(Predicted)
• CAS DataBase Reference: 5-BROMO-QUINOLIN-8-YLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-QUINOLIN-8-YLAMINE(53472-18-7)
• EPA Substance Registry System: 5-BROMO-QUINOLIN-8-YLAMINE(53472-18-7)

Safety Data

• Hazardous Substances Data: 53472-18-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
5-Bromo-Quinolin-8-Ylamine is used as an intermediate compound for creating new, more complex molecules. Its unique structure makes it a valuable component in the synthesis of various organic compounds.
Used in Pharmaceutical Research:
5-Bromo-Quinolin-8-Ylamine is utilized in pharmaceutical research, where its distinctive structure and properties contribute to the development of potential drug candidates. Its role in this field is mainly as a building block for more complex molecules with potential therapeutic applications.

InChI:InChI=1/C9H7BrN2/c10-7-3-4-8(11)9-6(7)2-1-5-12-9/h1-5H,11H2

Upstream product

• 33757-48-1 N-quinolin-8-yl-benzamide 
• 170891-76-6 α,α,α-trimethyl-N-(quinolin-8-yl)acetamide 
• 578-66-5 8-amino quinoline 
• 176967-80-9 5-bromo-8-nitroquinoline 

Downstream Products

• 1215767-84-2 5-bromo-7-chloroquinoline 
• 40000-20-2 5-bromo-1,10-phenanthroline 
• 16204-88-9 N-(5-bromoquinolin-8-yl)-4-methylbenzenesulfonamide 

Relevant articles and documents

Merging Photoredox Catalysis with Iron(III) Catalysis: C5-H Bromination and Iodination of 8-Aminoquinoline Amides in Water

A simple and efficient protocol for the iron(III)-catalyzed C5 halogenation of 8-aminoquinoline with potassium halides via a photoredox process was developed, affording desired products in good to excellent yields. This reaction features its mild and gree

Nickel-Catalyzed N, N-Diarylation of 8-Aminoquinoline with Large Steric Aryl Bromides and Fluorescence of Products

A simple and efficient methodology for the synthesis of large sterically hindered triarylamines in a single step was developed. A direct N,N-diarylation of 8-aminoquinoline with sterically hindered bromides, making use of inexpensive nickel as a catalyst and simple sodium salt as a base, gives the products in good to excellent yields. Various bromides and substituted 8-aminoquinolines are tolerated. Preliminary fluorescence results indicate that these sterically hindered and conjugated triarylamines may have some potential in material chemistry.

Visible light-induced mono-bromination of arenes with BrCCl3

A highly efficient and regioselective bromination of electron-rich arenes and heteroarenes using commercially available BrCCl3as a “Br” source has been developed. The reaction was performed in air under mild conditions with photocatalyst Ru(bpy)3Cl2·6H2O, avoiding the usage of strong acids and strong oxidants. Mono-brominated products were obtained with medium to excellent yields (up to 94%). This strategy has shown good compatibility and highpara-selectivity, which will facilitate the complicated synthesis.

New compound used as rearranged during transfection kinase inhibitor

The present invention relates to a compound, a pharmaceutical composition containing the compound, a preparation method of the compounds, and application of the same as a rearranged during transfection (RET) kinase inhibitor. The compound is a compound shown as formula (I), or a pharmaceutically acceptable salt, a prodrug, a solvent compound, a polymorph, an isomer and a stable isotope derivativethereof. The present invention also relates to the application of the compounds to treatment or prevention of RET kinase mediated related diseases like tumors and a method of using the compounds for the treatment of the diseases.

Iodine-catalyzed synthesis of N,N'-chelate organoboron aminoquinolate

We disclose a novel method for the synthesis of fluorescent N,N'-chelate organoboron compounds in high efficiency by treatment of aminoquinolates with NaBAr4/ R'COOH in the presence of an iodine catalyst. These compounds display high air and thermal stability. A possible catalytic mechanism based on the results of control experiments has been proposed. Fluorescence quantum yield of 3b is up to 0.79 in dichloromethane.

ALPHA, BETA-UNSATURATED AMIDE COMPOUND

An object of the present invention is to provide an α,β-unsaturated amide compound or a pharmaceutically acceptable salt or the like thereof having anticancer activity and the like. The α,β-unsaturated amide compound represented by the following formula (I) or a pharmaceutically acceptable salt or the like thereof has anticancer activity and the like: [wherein, "A" represents optionally substituted heterocyclic diyl, R1 represents hydrogen atom or optionally substituted lower alkyl, R2 represents optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted aliphatic heterocyclic group or optionally substituted aromatic heterocyclic group, X represents -O-, -S-, -SO2-, -NRX1- (wherein, RX1 represents hydrogen atom or lower alkyl), -CHRX2- (wherein, RX2 represents hydrogen atom or hydroxy), -CH=CH-, -CO- or -NH-CO-, and n1 and n2 are the same or different, and each represents 0 or 1].

Cu-mediated selective bromination of aniline derivatives and preliminary mechanism study

A simple and efficient bromination of aniline, aniline derivatives, and analogs have been developed. Forty three examples were given and the highest yield reached was 98%. Different substrates including substituted aniline, pyridin-amine, N-substituted aniline, N,N-disubstituted aniline, N-phenyl-amide, N-phenyl-sulfonamide, and nitrogen-containing heterocycles were all reactive and selectively generated desired bromo-products. The method can be applied to synthesize drug intermediate and quinoxaline derivatives.

Structure-activity relationships, biological evaluation and structural studies of novel pyrrolonaphthoxazepines as antitumor agents

Microtubule-targeting agents (MTAs) are a class of clinically successful anti-cancer drugs. The emergence of multidrug resistance to MTAs imposes the need for developing new MTAs endowed with diverse mechanistic properties. Benzoxazepines were recently identified as a novel class of MTAs. These anticancer agents were thoroughly characterized for their antitumor activity, although, their exact mechanism of action remained elusive. Combining chemical, biochemical, cellular, bioinformatics and structural efforts we developed improved pyrrolonaphthoxazepines antitumor agents and their mode of action at the molecular level was elucidated. Compound 6j, one of the most potent analogues, was confirmed by X-ray as a colchicine-site MTA. A comprehensive structural investigation was performed for a complete elucidation of the structure-activity relationships. Selected pyrrolonaphthoxazepines were evaluated for their effects on cell cycle, apoptosis and differentiation in a variety of cancer cells, including multidrug resistant cell lines. Our results define compound 6j as a potentially useful optimized hit for the development of effective compounds for treating drug-resistant tumors.

Iron(III)-catalyzed highly regioselective halogenation of 8-amidoquinolines in water

A simple protocol of iron(III)-catalyzed halogenation of 8-amidoquinolines in water under mild conditions was developed, affording the 5-halogenlated products in good to excellent yields up to 98%. The reaction mechanism most likely involves a single-elec

A general method for the metal-free, regioselective, remote C-H halogenation of 8-substituted quinolines

An operationally simple and metal-free protocol for geometrically inaccessible C5-H halogenation of a range of 8-substituted quinoline derivatives has been established. The reaction proceeds under air, with inexpensive and atom economical trihaloisocyanuric acid as a halogen source (only 0.36 equiv.), at room temperature. Exceptionally high generality with respect to quinoline is observed, and in most instances, the reaction proceeded with complete regioselectivity. Quinoline with a variety of substituents at the 8-position gave, exclusively, the C5-halogenated product in good to excellent yields. Phosphoramidates, tertiary amides, N-alkyl/N,N-dialkyl, and urea derivatives of quinolin-8-amine as well as alkoxy quinolines were halogenated at the C5-position via remote functionalization for the first time. This methodology provides a highly economical route to halogenated quinolines with excellent functional group tolerance, thus providing a good complement to existing remote functionalization methods of quinolin-8-amide derivatives and broadening the field of remote functionalization. The utility of the method is further showcased through the synthesis of several compounds of biological and pharmaceutical interest.