8-Hydroxyquinoline-N-oxide Chemical Properties

Melting point:

135-138 °C (lit.)

Boiling point:

267 °C(lit.)

Density 

1.2480 (rough estimate)

refractive index 

1.5050 (estimate)

Flash point:

139 °C

storage temp. 

Inert atmosphere,2-8°C

solubility 

Soluble in Acetone, Chloroform, Dichloromethane, Ethyl Acetate and Methanol

pka

6.03±0.30(Predicted)

form 

Solid

color 

Yellow

BRN 

128737

InChI

InChI=1S/C9H7NO2/c11-8-5-1-3-7-4-2-6-10(12)9(7)8/h1-6,11H

InChIKey

FJKUOCCQEBLPNX-UHFFFAOYSA-N

SMILES

[N+]1([O-])=C2C(C=CC=C2O)=CC=C1

CAS DataBase Reference

1127-45-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

N,Xi

Risk Statements 

50/53-36/37/38

Safety Statements 

60-61-24/25-22-36/37/39-27-26

RIDADR 

UN 3077 9/PG 3

WGK Germany 

3

RTECS 

VC8238500

F 

3-10

HS Code 

29334900

MSDS

• Language:English Provider:8-Hydroxyquinoline-N-oxide
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

8-Hydroxyquinoline-N-oxide Usage And Synthesis

Description

A quinoline derivative that displays mutagenic activity. It suppresses luminescence of an indicator bacterium that is named Photobacterium phosphoreum. This chemical forms two kinds of complexes with palladium (II) and Gold (III). One kind is an ion-associated compound containing hydrogen bond and hte other is the six membered metal chelates containing metal-oxygen bonds.

Chemical Properties

Yellow Crystalline Solid

Uses

A quinoline derivative; shows mutagenic activity.

Definition

ChEBI: 8-hydroxyquinoline N-oxide is a quinoline N-oxide carrying a hydroxy substituent at position 8. It is a monohydroxyquinoline and a quinoline N-oxide. It is functionally related to a quinolin-8-ol. It is a conjugate acid of an 8-hydroxyquinoline N-oxide(1-).

General Description

8-Quinolinol N-oxide is a toxicant which can suppress luminescence of an indicator bacterium Photobacterium phosphoreum. It forms two types of complexes with gold(III) and palladium(II): type I are ion-associated compounds containing hydrogen bond and the other is the six-membered metal chelates containing metal-oxygen bonds.

Synthesis

8-hydroxyquinoline-N-oxide was synthesized from 8-hydroxyquinoline. A stirred solution of 8-hydroxyquinoline (25.00 g, 172.2 mmol) in 550 ml of CHCl₃ was cooled to 0° C., and 3 -chloroperoxybenzoic acid (40.00 g, 80% Tech. grade *0.231 mmol=0.185 mmol) was added slowly over 3 minutes. The solution was kept at 0° C. and stirred for 3 hours. During this period, the 3-chlorobenzoic acid byproduct precipitated. The 3-chlorobenzoic acid was removed by filtration and the orange filtrate was concentrated to dryness and the remaining solid was triturated with 2% NH40 H (2*200 ml). The solid was isolated on a frit and washed with H₂O.

References

[1] Naunyn-Schmiedeberg's Archives of Pharmacology, 1999, vol. 359, # 3, p. 168 - 177
[2] ChemCatChem, 2015, vol. 7, # 23, p. 3903 - 3910
[3] Patent: US2003/97000, 2003, A1
[4] Patent: US6617336, 2003, B1
[5] Organic Letters, 2011, vol. 13, # 14, p. 3556 - 3559

8-Hydroxyquinoline-N-oxide(1127-45-3)Related Product Information

• 8-HYDROXYOCTANOIC ACID
• 3-CHLOROPYRIDINE N-OXIDE
• ISOQUINOLINE N-OXIDE
• (4-METHOXY-PYRIDIN-2-YL)-METHANOL
• 4-(4-Methoxyphenyl)butyric acid
• 4-(4-HYDROXYPHENYL)BUTANOIC ACID
• 8-Hydroxyquinoline
• OXINE-COPPER
• 8-Hydroxyquinoline sulfate monohydrate
• Quinoline-N-oxide
• 8-Hydroxyquinoline-N-oxide
• QUINOLINE N-OXIDE HYDRATE
• Quinoline
• CHEMBRDG-BB 5175127
• 4-HYDROXYQUINOLINE-N-OXIDE
• 2-HEPTYL-4-HYDROXYQUINOLINE-N-OXIDE,2-HEPTYL-4-HYDROXYQUINOLINE-1-OXIDE
• nonyl-4-hydroxyquinoline-N-oxide
• 5-[(2-Hydroxy-3,5-dinitrophenyl)azo]-8-hydroxyquinoline 1-oxide