7613-19-6

Basic information

• Product Name: 5-NITROQUINOLINE 1-OXIDE
• Synonyms: 5-NITROQUINOLINE 1-OXIDE;5-nitro-1-oxidoquinolin-1-ium
• CAS NO: 7613-19-6
• Molecular Formula: C₉H₆N₂O₃
• Molecular Weight: 190.16
• Mol File: 7613-19-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 163-164 °C(Solv: toluene (108-88-3))
• Boiling Point: 387.6°C at 760 mmHg
• Flash Point: 188.2°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 7.25E-06mmHg at 25°C
• Refractive Index: 1.659
• PKA: -0.70±0.30(Predicted)
• CAS DataBase Reference: 5-NITROQUINOLINE 1-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-NITROQUINOLINE 1-OXIDE(7613-19-6)
• EPA Substance Registry System: 5-NITROQUINOLINE 1-OXIDE(7613-19-6)

Safety Data

• Hazardous Substances Data: 7613-19-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H6N2O3/c12-10-6-2-3-7-8(10)4-1-5-9(7)11(13)14/h1-6H

Upstream product

• 1613-37-2 Quinoline N-oxide 
• 7664-93-9 sulfuric acid 
• 7446-11-9 sulfur trioxide 

Downstream Products

• 13067-94-2 2-chloro-5-nitroquinoline 
• 40106-98-7 4-chloro-5-nitroquinoline 
• 16238-73-6 4,5-dinitroquinoline 1-oxide 
• 6938-27-8 5-nitro-2<1H>quinolinone 
• 77738-80-8 2-methoxy-5-nitroquinoline 
• 23536-75-6 4-Hydroxy-5-nitrochinolin 
• 1374107-32-0 5-amino-2-(4-fluorophenyl)quinoline 
• 1374108-73-2 C₁₅H₉FN₂O₂ 
• 1620101-00-9 8-(4-methylphenylsulfonamido)-5-nitroquinoline N-oxide 
• 607-34-1 5-nitroquinoline 
• 1027402-28-3 (E)-5-nitro-2-styrylquinoline 
• 116632-28-1 2-bromo-5-nitroquinoline 
• 611-34-7 5-Aminoquinoline 
• 61317-32-6 5-aminoquinolin-2(1H)-one 

Relevant articles and documents

Nitration of quinoline 1-oxide: Mechanism of regioselectivity

The acidity dependence of orientation in the nitration of quinoline 1- oxide was investigated by using the trifluoromethanesulfonic acid (TFSA)- trifluoroacetic acid (TFA) system and the antimony pentafluoride (SbF5)- TFSA system. These systems provide a wider range of acidity than that of aqueous sulfuric acid. Comparison of the behavior of quinoline 1-oxide and 1- methoxyquinolinium triflate in acidic and neutral media demonstrated that O- protonated quinoline 1-oxide is nitrated at the 5- and 8-positions, and the free (unprotonated) molecule is nitrated at the 4-position. This result is consistent with theoretical expectation. It was also discovered that nitration at the 5-position increasingly predominates over that at the 8- position as the acidity is increased.