99465-03-9

Basic information

• Product Name: 6-Bromo-2-oxo-1,2-dihydro-3-quinolinecarbonitrile
• Synonyms: 6-Bromo-2-oxo-1,2-dihydro-3-quinolinecarbonitrile;6-Bromo-1,2-dihydro-2-oxoquinoline-3-carbonitrile
• CAS NO: 99465-03-9
• Molecular Formula: C10H5BrN2O
• Molecular Weight: 249.066
• Mol File: 99465-03-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: >300°
• Boiling Point: 446°C at 760 mmHg
• Flash Point: 223.5°C
• Appearance: /
• Density: 1.76g/cm³
• Vapor Pressure: 3.77E-08mmHg at 25°C
• Refractive Index: 1.694
• CAS DataBase Reference: 6-Bromo-2-oxo-1,2-dihydro-3-quinolinecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromo-2-oxo-1,2-dihydro-3-quinolinecarbonitrile(99465-03-9)
• EPA Substance Registry System: 6-Bromo-2-oxo-1,2-dihydro-3-quinolinecarbonitrile(99465-03-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 99465-03-9(Hazardous Substances Data)

Usage

General Description

6-Bromo-2-oxo-1,2-dihydro-3-quinolinecarbonitrile is a chemical compound with the molecular formula C10H5BrN2O. It is a quinoline derivative and contains a bromine atom, a cyano group, and a carbonyl group. 6-Bromo-2-oxo-1,2-dihydro-3-quinolinecarbonitrile is commonly used in organic synthesis and pharmaceutical research as a building block for the synthesis of various pharmaceuticals and bioactive molecules. It has been reported to exhibit antibacterial and antifungal activities, making it potentially useful in the development of new antimicrobial agents. Additionally, this compound has been studied for its potential antitumor and antiviral properties. Its unique structure and reactivity make it a valuable intermediate for the synthesis of diverse chemical compounds with potential biological and medicinal applications.

InChI:InChI=1/C10H5BrN2O/c11-8-1-2-9-6(4-8)3-7(5-12)10(14)13-9/h1-4H,(H,13,14)

Upstream product

• 36926-82-6 2-oxo-1,2-dihydroquinoline-3-carbonitrile 

Downstream Products

• 99465-04-0 6-bromo-2-chloro-3-cyanoquinoline 

Relevant articles and documents

2(1H)-Quinolinones with cardiac stimulant activity. 1. Synthesis and biological activities of (six-membered heteroaryl)-substituted derivatives

A series of (six-membered heteroaryl)-substituted 2(1H)-quinolinones was synthesized, and structure-activity relationships for cardiac stimulant activity were determined. Most compounds were prepared by acidic hydrolyisis of a heteroaryl-2-methoxyquinoline obtained by palladium-catalyzed cross-coupling methodology. Direct reaction of a pyridinylzinc reagent with a 6-haloquinolinone also proved successful. In anesthetized dogs, 6-pyridin-3-yl-2(1H)-quinolinone (3; 50 μg/kg) displayed greater inotropic activity (percentage increase in dP/dt max) than positional isomers, and potency was maintained with either mono- or di- alkylpyridinyl substituents. Introduction of a 4- or 7- methyl group into 3 reduced inotropic activity, whereas the 8-isomer proved to be the most potent member of the series. Compound 26 and the 2,6-dimethylpyridinyl analogue (27 were approximately 6 and 3 times more potent than milrinone. Several quinolinones displayed positive inotropic activity (decrease in QA interval) in conscious dogs after oral administration (1 mg/kg), and 26, 27 were again the most potent members of the series. Compound 27 (0.25, 0.5, 1.0 mg/kg po) demonstrated dose-related cardiac stimulant activity, which was maintained for at least 4 h. No changes in heart rate were observed. Compounds 3, 4, 26, and 27 also selectively stimulated the force of contraction, rather than heart rate, in the dog heart-lung preparation. For a 50% increase in dP/dt max with 27, heart rate changed by less than 10 beats/min. In norepinephrine contracted rabbit femoral artery and saphenous vein, 27 produced dose related (5 x 10-7 to 5 x 10-4 M) vasorelaxant activity. The combined cardiac stimulant and vasodilator properties displayed by 27, coupled with a lack of effect on heart rate, should be beneficial for the treatment of congestive heart failure.