64965-47-5

Basic information

• Product Name: 3-BROMO-4-HYDROXYQUINOLINE
• Synonyms: 3-BROMO-4-HYDROXYQUINOLINE;3-BROMOQUINOLIN-4-OL
• CAS NO: 64965-47-5
• Molecular Formula: C₉H₆BrNO
• Molecular Weight: 224.05
• Mol File: 64965-47-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 282 °C
• Boiling Point: 290.6°C at 760 mmHg
• Flash Point: 129.6°C
• Appearance: /
• Density: 1.666g/cm³
• Vapor Pressure: 0.00205mmHg at 25°C
• Refractive Index: 1.654
• PKA: 1.67±0.50(Predicted)
• CAS DataBase Reference: 3-BROMO-4-HYDROXYQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-4-HYDROXYQUINOLINE(64965-47-5)
• EPA Substance Registry System: 3-BROMO-4-HYDROXYQUINOLINE(64965-47-5)

Safety Data

• Hazard Codes: T
• Statements: 25-41
• Safety Statements: 26-39-45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 64965-47-5(Hazardous Substances Data)

Usage

General Description

3-Bromo-4-hydroxyquinoline is a chemical compound with the molecular formula C9H6BrNO. It is a brominated derivative of 4-hydroxyquinoline and is used as a reagent in organic synthesis and pharmaceutical research. It is a yellow to brown solid at room temperature and is soluble in organic solvents such as ethanol and acetone. 3-BROMO-4-HYDROXYQUINOLINE is known for its antimicrobial and antifungal properties, and it is also used in the production of agrochemicals and pharmaceuticals. 3-Bromo-4-hydroxyquinoline is an important building block for the synthesis of various biologically active compounds and has potential applications in the field of medicinal chemistry.

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

Upstream product

• 611-36-9 quinolin-4-ol 
• 495409-73-9 3-bromo-4-hydroxy-quinoline-2-carboxylic acid methyl ester 
• 861357-59-7 3-bromo-4-hydroxy-quinoline-2-carboxylic acid 

Downstream Products

• 74575-17-0 3-bromo-4-chloroquinoline 
• 41320-96-1 3,4-dibromoquinoline 
• 36255-25-1 3-bromo-4-methoxy-quinoline 
• 942904-93-0 3-(4-methylbenzenesulfanyl)-4-hydroxy-quinoline 
• 1312180-41-8 3-bromo-4-(4'-methoxyphenyl)quinoline 
• 1312180-44-1 3,4-bis(4'-methoxyphenyl)quinoline 
• 1312180-98-5 3-(4'-methoxyphenyl)-4-(trans-hepten-1-yl)quinoline 
• 1312180-96-3 3-(4'-methoxyphenyl)-4-(2'-thienyl)quinoline 
• 1312180-92-9 4-(4'-methoxyphenyl)-3-(2'-thienyl)quinoline 
• 1312180-94-1 3-(4'-methoxyphenyl)-4-(3'-nitrophenyl)quinoline 
• 1312180-90-7 4-(4'-methoxyphenyl)-3-(3'-nitrophenyl)quinoline 
• 1360598-49-7 3-phenylthioquinolin-4-ol 
• 1360598-50-0 3-(phenylsulfonyl)quinoline-4-ol 
• 1360598-51-1 4-chloro-3-(phenylsulfonyl)quinoline 

Relevant articles and documents

Catalytic atroposelective dynamic kinetic resolutions and kinetic resolutions towards 3-arylquinolinesviaSNAr

Herein we report the catalytic atroposelective syntheses of pharmaceutically relevant 3-arylquinolinesviathe nucleophilic aromatic substitution (SNAr) of thiophenols into 3-aryl-2-fluoroquinolines mediated by catalytic amounts of Cinchona alkaloid-derived ureas. These reactions displayed a spectrum of dynamic kinetic resolution (DKR) and kinetic resolution (KR) characters depending upon the stereochemical stability of the starting material. Low barrier substrates proceededviaDKR while higher barrier substrates proceededviaKR. On the other hand, substrates with intermediate stabilities displayed hallmarks of both DKR and KR. Finally, we also show that we can functionalize the atropisomerically enriched quinolines into pharmaceutically privileged scaffolds with minimal observed racemization.