22246-16-8

Basic information

• Product Name: 3,4-Dihydro-6-nitro-2(1H)-quinolinone
• Synonyms: 3,4-Dihydro-6-nitro-2(1H)-quinolinone;3,4-Dihydro-6-nitro-carbostyril;6-Nitro-1,2,3,4-tetrahydrochinolin-2-one;6-Nitro-1,3,4-trihydroquinolin-2-one;3,4-Dihydro-6-nitro-1H-quinolin-2-one;6-Nitro-3,4-dihydro-1H-quinolin-2-one;6-nitro-3,4-dihydrocarbostyril;6-nitro-1,2,3,4-tetrahydroquinolin-2-one
• CAS NO: 22246-16-8
• Molecular Formula: C₉H₈N₂O₃
• Molecular Weight: 192.18
• Product Categories: Aromatics Compounds;Aromatics;Heterocycles
• Mol File: 22246-16-8.mol
• Article Data: 20

Chemical Properties

• Melting Point: 201-2020C
• Boiling Point: 420.3 °C at 760 mmHg
• Flash Point: 208 °C
• Appearance: /
• Density: 1.366 g/cm³
• Vapor Pressure: 2.85E-07mmHg at 25°C
• Refractive Index: 1.605
• Storage Temp.: Store below -20C
• Solubility: DMSO, Methanol
• PKA: 13.45±0.20(Predicted)
• CAS DataBase Reference: 3,4-Dihydro-6-nitro-2(1H)-quinolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dihydro-6-nitro-2(1H)-quinolinone(22246-16-8)
• EPA Substance Registry System: 3,4-Dihydro-6-nitro-2(1H)-quinolinone(22246-16-8)

Safety Data

• Hazard Codes: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 22246-16-8(Hazardous Substances Data)

Usage

Chemical Properties

Off-white to yellowish brown solid

Uses

3,4-Dihydro-6-nitro-2(1H)-quinolinone is a useful intermediate for organic synthesis. It is used in the synthesis of triazolyl dihydroquinoliinones with anticonvulsant and antidepressant activity.

InChI:InChI=1/C9H8N2O3/c12-9-4-1-6-5-7(11(13)14)2-3-8(6)10-9/h2-3,5H,1,4H2,(H,10,12)

Upstream product

• 553-03-7 3,4-dihydro-2(1H)-quinolone 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 62-53-3 aniline 
• 3460-04-6 3-chloro-N-phenylpropionamide 

Downstream Products

• 22246-13-5 6-amino-3,4-dihydro-1H-quinolin-2-one 
• 296759-27-8 6,8-dinitro-3,4-dihydroquinolin-2-one 
• 2229039-45-4 (E)-6-((2-amino-4-hydroxy-5-methylphenyl)diazenyl)-3,4-dihydroquinolin-2(1H)-one 

Relevant articles and documents

Novel 3,4-dihydroquinolin-2(1H)-one derivatives as dual inhibitor targeting AKR1B1/ROS for treatment of diabetic complications: Design, synthesis and biological evaluation

AKR1B1 (Aldose reductase) has been used as therapeutic intervention target for treatment of diabetic complications over 50 years, and more recently for inflammation and cancer. However, most developed small molecule inhibitors have the defect of low bioac

Tetrahydroquinolinyl phosphinamidates and phosphonamidates enhancing tolerance towards drought stress in crops via interaction with ABA receptor proteins

New phosphorous-containing lead structures against drought stress in crops interacting with RCAR/(PYR/PYL) receptor proteins were identified starting from in-depth SAR studies of related sulfonamide lead structures and protein docking studies. A converging 6-step synthesis via phosphinic chlorides and phosphono chloridates as key intermediates afforded envisaged tetrahydroquinolinyl phosphinamidates and phosphonamidates. Whilst tetrahydroquinolinyl phosphonamidates 13a,b exhibited low to moderate target affinities, the corresponding tetrahydroquinolinyl phosphinamidates 12a,b revealed confirmed strong affinities for RCAR/ (PYR/PYL) receptor proteins in Arabidopsis thaliana on the same level as essential plant hormone abscisic acid (ABA) combined with promising efficacy against drought stress in vivo (broad-acre crops wheat and canola).

SUBSTITUTED OXOTETRAHYDROQUINOLINYLPHOSPHINIC ACID AND PHOSPHINIC ACID AMIDES OR SALTS THEREOF AND USE THEREOF TO INCREASE STRESS TOLERANCE IN PLANTS

The invention relates to substituted oxotetrahydroquinolinylphosphin- and -phosphonamides of the general formula (I) and salts thereof where the radicals of the formula (I) are each as defined in the description for enhancing stress tolerance in plants to abiotic stress, and for enhancing plant growth and/or for increasing plant yield.