8-Hydroxyquinoline-2-carboxaldehyde

8-Hydroxyquinoline-2-carboxaldehyde Property

Melting point:

97-100 °C

Boiling point:

392.2±22.0 °C(Predicted)

Density 

1.364±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

9.27±0.10(Predicted)

form 

Crystalline Powder

color 

Yellow

BRN 

127519

InChI

InChI=1S/C10H7NO2/c12-6-8-5-4-7-2-1-3-9(13)10(7)11-8/h1-6,13H

InChIKey

SLBPIHCMXPQAIQ-UHFFFAOYSA-N

SMILES

N1C2C(=CC=CC=2O)C=CC=1C=O

CAS DataBase Reference

14510-06-6

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HS Code 

29339900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

8-Hydroxyquinoline-2-carboxaldehyde Chemical Properties,Usage,Production

Chemical Properties

yellow crystalline powder

Uses

8-Hydroxy-2-quinolinecarboxaldehyde (8-hydroxyquinoline-2-carbaldehyde) may be used in the preparation of:

• 8-hydroxy-2-quinoline-1-aminopyrene by Schiff-base reaction with 1-aminopyrene
• (E)-2-((2-(pyridin-2-yl)hydrazono)methyl)quinolin-8-ol by coupling with 2-hydrazinopyridine
• 8-hydroxyquinoline-2-carbaldehyde oxime
• 2-[(8-Hydroxyquinoline)-2-methylaminoethyl]-β-D-glucopyranoside

Definition

ChEBI: 8-hydroxyquinoline-2-carbaldehyde is a hydroxyquinoline.

General Description

8-Hydroxy-2-quinolinecarboxaldehyde can be prepared from 2-methylquinolin-8-ol via oxidation using selenium dioxide.

Synthesis

General procedure for the synthesis of 8-hydroxyquinoline-2-carbaldehyde from 8-hydroxyquinaldine: Preparation of 3,3'-(1E,1'E)-(propane-1,3-diylbis(aza-1-yl-1-ylidene))bis(methyl-1-ylidene-1-ylidene)diquinolin-8-ol (H2PBIQ). A mixture of 8-hydroxy-2-methylquinoline (4 g, 25 mmol), selenium dioxide (3.5 g, 31 mmol), water (3 mL), and 1,4-diethylene glycol (300 mL) was stirred for 24 h at 80 °C under nitrogen protection. After completion of the reaction, the mixture was cooled, filtered and the filtrate evaporated. The resulting solid was purified by silica gel column chromatography (unfolding solvent was petroleum ether: ethyl acetate, 95:5, v/v) to afford pure yellow needle-like crystals of 8-hydroxyquinoline-2-carbaldehyde. The yield was 90%; 1H NMR (400 MHz, CDCl3): δ10.25 (s, 1H), 8.35 (d, J=8.5 Hz, 1H), 8.18 (s, 1H), 8.09 (d, J=8.5 Hz, 1H), 7.66 (t, J=8.0 Hz, 1H), 7.46 (d, J=8.2 Hz, 1H), and 7.31 (d, J=7.7Hz, 1H).

References

[1] RSC Advances, 2015, vol. 5, # 129, p. 107012 - 107019
[2] Inorganic Chemistry Communications, 2014, vol. 47, p. 13 - 16
[3] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 864 - 879
[4] Inorganic Chemistry, 2013, vol. 52, # 11, p. 6346 - 6353
[5] Dalton Transactions, 2014, vol. 43, # 26, p. 10164 - 10174