ISOQUINOLINE N-OXIDE Chemical Properties

Melting point:

103-105 °C(lit.)

Boiling point:

170°C 3mm

Density 

1.1555 (rough estimate)

refractive index 

1.4500 (estimate)

Flash point:

170°C/3mm

storage temp. 

Inert atmosphere,Room Temperature

pka

0.74±0.30(Predicted)

form 

powder to crystal

color 

Light yellow to Yellow to Orange

Sensitive 

Hygroscopic

BRN 

114345

InChIKey

RZIAABRFQASVSW-UHFFFAOYSA-N

CAS DataBase Reference

1532-72-5(CAS DataBase Reference)

Safety Information

Risk Statements 

36/38

Safety Statements 

24/25

WGK Germany 

3

HS Code 

2933499090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

ISOQUINOLINE N-OXIDE Usage And Synthesis

Chemical Properties

cream to brown powder or chunks

Uses

Isoquinoline n-oxide an isoquinoline metabolite.

Definition

ChEBI: Isoquinoline N-oxide is a member of isoquinolines.

Synthesis Reference(s)

Tetrahedron, 50, p. 12185, 1994 DOI: 10.1016/S0040-4020(01)89569-7

General Description

Photochemical isomerization of isoquinoline N-oxide in methanol or water has been investigated by steady-light irradiation and flash spectroscopy. It is a useful intermediate for isoquinoline derivatives. It causes the oxidation of fullerene C₆₀ under ultrasonic irradiation in air.

Synthesis

In a 50 mL round-bottomed flask, 1.29 g of isoquinoline, 1.1 g of 35% mass fraction of hydrogen peroxide, 5% mass fraction of perfluorosulfonic acid resin, and 10 mL of water as solvent were sequentially added. The resulting mixture was placed in a 30 W/20 kHz ultrasonic reactor for 15 min. After the reaction was completed, the perfluorosulfonic acid resin catalyst was removed from the system by filtration, the water in the solvent was removed by distillation under reduced pressure, and finally the target product was purified by recrystallization to give 1.39 g of isoquinoline-N-oxide in 96% yield.

References

[1] Organic Letters, 2018, vol. 20, # 8, p. 2346 - 2350
[2] Heterocyclic Communications, 2007, vol. 13, # 1, p. 25 - 28
[3] Chemistry - A European Journal, 2014, vol. 20, # 2, p. 559 - 563
[4] Patent: CN108003098, 2018, A. Location in patent: Paragraph 0085; 0086; 0087
[5] Journal of the American Chemical Society, 2009, vol. 131, p. 3291 - 3306

ISOQUINOLINE N-OXIDE(1532-72-5)Related Product Information

• Isoquinoline
• Isoquinoline-4-carboxylic acid
• 1-ISOQUINOLINEMETHANOL
• 6-isoquinolinecarboxylic acid
• 3-isoquinolinecarboxaldehyde
• ISOQUINOLINE-1-CARBALDEHYDE
• 8-Isoquinolinecarbonitrile(9CI)
• ISOQUINOLINE-1-CARBOXYLIC ACID METHYL ESTER
• ETHYL ISOQUINOLINE-3-CARBOXYLATE
• Isoquinoline-3-carboxylic acid
• ISOQUINOLINE-5-CARBOXYLIC ACID
• 7-Isoquinolinecarboxaldehyde (6CI,9CI)
• p-[2-(3,4-dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isoquinolyl)ethyl]benzenesulphonamide
• 7-isoquinolinecarboxylic acid
• Methyl 3-isoquinolinecarboxylate
• ISOQUINOLINE-5-CARBALDEHYDE
• ISOQUINOLINE-3-CARBOXYLIC ACID
• Isoquinoline-1-carboxylic acid