1810-66-8

Basic information

• Product Name: 6-BROMO-2(1H)-QUINOLONE
• Synonyms: 6-BROMOQUINOLIN-2(1H)-ONE;6-BROMO-2-QUINOLONE;6-BROMO-2-HYDROXYQUINOLINE;6-BROMO-2(1H)-QUINOLONE;6-Bromo-2(1H)-quinolinone;6-Bromo-2-quinolinol;6-Bromocarbostyril;6-Bromo-2-quinolinone
• CAS NO: 1810-66-8
• Molecular Formula: C₉H₆BrNO
• Molecular Weight: 224.05
• Product Categories: Aromatics Compounds;CHIRAL CHEMICALS;Aromatics;Heterocycles
• Mol File: 1810-66-8.mol
• Article Data: 24

Chemical Properties

• Melting Point: 278-280?C
• Boiling Point: 393.766 °C at 760 mmHg
• Flash Point: 191.943 °C
• Appearance: Beige solid
• Density: 1.62 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.63
• Storage Temp.: Refrigerator
• Solubility: DMSO
• PKA: 10.76±0.70(Predicted)
• CAS DataBase Reference: 6-BROMO-2(1H)-QUINOLONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-2(1H)-QUINOLONE(1810-66-8)
• EPA Substance Registry System: 6-BROMO-2(1H)-QUINOLONE(1810-66-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 1810-66-8(Hazardous Substances Data)

Usage

Chemical Properties

Beige Solid

Uses

6-Bromo-2(1H)-quinolinone is a useful intermediate for the synthesis of other quinoline derivatives.

InChI:InChI=1/C9H6BrNO/c10-7-2-3-8-6(5-7)1-4-9(12)11-8/h1-5H,(H,11,12)

Upstream product

• 6563-11-7 6-bromoquinoline-N-oxide 
• 99455-05-7 2-methoxy-6-bromoquinoline 
• 71205-21-5 methyl (E)-3-(2-amino-5-bromophenyl)prop-2-enoate 
• 1132940-92-1 (E)-N-(4-bromophenyl)-3-methoxyacrylamide 
• 5332-25-2 6-bromoquinoline 
• 106-40-1 4-bromo-aniline 
• 140-88-5 ethyl acrylate 
• 1035669-79-4 C₁₁H₁₀BrNO 
• 7664-93-9 sulfuric acid 
• 327058-51-5 N-(4-bromophenyl)-(E)-3-ethoxyacrylamide 
• 914918-89-1 C₁₃H₁₈BrNO₃ 
• 577967-86-3 N-(4-bromo-phenyl)-3-ethoxy-acrylamide 
• 6931-16-4 2-methoxy-quinoline 
• 66416-72-6 4-bromo-2-iodoaniline 

Downstream Products

• 77514-31-9 2,6-di-bromoquinoline 
• 328954-96-7 6-(2,3-Difluoro)phenyl-4-trifluoromethyl-2(1H)-quinolinone 
• 300811-62-5 2-(benzyloxy)-6-bromoquinoline 
• 63124-11-8 2-oxo-1H-quinoline-6-carbonitrile 
• 1810-71-5 6-bromo-2-chloroquinoline 
• 78060-54-5 2-chloroquinoline-6-carbonitrile 
• 70639-78-0 1,2-dihydro-2-oxo-6-quinolinecarboxylic acid 
• 68882-86-0 2-oxo-1,2-dihydroquinoline-6-carboxylic acid methyl ester 
• 791626-59-0 2-chloroquinoline-6-carbaldehyde 
• 1071467-79-2 2-(2-(2-(6-(4-(tert-butoxycarbonyl(methyl)amino)phenyl)quinolin-2-yloxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate 
• 1071467-87-2 C₃₃H₄₈N₂O₆Si 
• 1071467-73-6 C₃₀H₃₄N₂O₆S 
• 1071467-86-1 C₂₈H₄₀N₂O₄Si 
• 1071467-78-1 4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)quinolin-6-yl)phenyl(methyl)carbamate 

Relevant articles and documents

Aminoquinoline-rhodium(II) conjugates as src-family SH3 ligands

High-affinity, selective ligands are sought for a variety of biomolecules but are particularly difficult to generate in the protein-protein interaction space. Rhodium(II) conjugates provide a structure-based approach to improved affinity and specificity f

Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinolineN-oxides

Quinolin-2(1H)-ones are one of the important classes of compounds due to their prevalence in natural products and in pharmacologically useful compounds. Here we present an unconventional and hitherto unknown photocatalytic approach to their synthesis from easily available quinoline-N-oxides. This reagent free highly atom economical photocatalytic method, with low catalyst loading, high yield and no undesirable by-product, provides an efficient greener alternative to all conventional synthesis reported to date. The robustness of the methodology has been successfully demonstrated with easy scaling up to the gram scale.

Scalable and Practical Synthesis of Halo Quinolin-2(1H)-ones and Quinolines

A practical and scalable synthesis of halo quinolin-2(1H)-ones is presented. The heterocycles are easily accessed from inexpensive halo anilines in a two-step sequence. The anilines are acylated with methyl 3,3-dimethoxypropionate under basic conditions in quantitative yields. The crude amides undergo cyclization in sulfuric acid to the desired halo quinolin-2(1H)-ones in 28-93% yield (2 steps). The synthetic sequence was successfully applied on 800 g scale. Anilines with strong electron withdrawing or electron donating groups were poor substrates for this procedure. 6-Iodoquinolin-2(1H)-one and 6-bromo-8-iodoquinolin-2(1H)-one were further functionalized to obtain quinolines substituted with various functional groups.