8-HYDROXY-QUINOLINE-5-CARBALDEHYDE

8-HYDROXY-QUINOLINE-5-CARBALDEHYDE Property

Melting point:

178 °C

Boiling point:

383.1±22.0 °C(Predicted)

Density 

1.364±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

3.88±0.10(Predicted)

color 

Green

InChI

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

InChIKey

LIADJWREMDHKHQ-UHFFFAOYSA-N

SMILES

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

Safety

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

8-HYDROXY-QUINOLINE-5-CARBALDEHYDE Chemical Properties,Usage,Production

Uses

8-Hydroxyquinoline-5-carbaldehyde is used in preparation of Polycyclic compounds.

Synthesis

8-Hydroxyquinoline (5 g, 0.034 mol) was dissolved in ethanol (50 mL), followed by the addition of sodium hydroxide (10 g, 0.25 mol) dissolved in water (15 mL). The mixed solution was heated to reflux and trichloromethane was added slowly and dropwise over 30 minutes. After continuing the reflux reaction for 20 h, ethanol and unreacted trichloromethane were removed by distillation under reduced pressure. The residue was dissolved in water (150 mL) and the pH was adjusted to slightly acidic with dilute hydrochloric acid. The resulting yellow solid was extracted with dichloromethane and the extract was purified by column chromatography (silica gel as stationary phase and dichloromethane/methanol as eluent) to give 8-hydroxyquinoline-5-carbaldehyde as a final white solid (115 mg, 0.67 mmol). The structure of the product was confirmed by 1H-NMR (CDCl3, 400 MHz) and 13C-NMR (DMSO-d6, 400 MHz): 1H-NMR δ = 10.16 (s, 1H), 9.71 (dd, 1H, J = 1.6Hz, 8.4Hz), 8.89 (dd, 1H, J = 1.6Hz, 4.0Hz), 8.02 (d , 1H, J = 8.0 Hz), 7.69 (q, 1H, J = 4.0 Hz), 7.30 (d, 1H, J = 8.0 Hz); 13C-NMR δ = 193.1, 160.5, 149.9, 141.1, 138.9, 133.9, 127.7, 125.5, 123.4, 111.7.

References

[1] Journal of Coordination Chemistry, 2012, vol. 65, # 9, p. 1632 - 1644
[2] Journal of Organic Chemistry, 2011, vol. 76, # 10, p. 3774 - 3781
[3] Journal of the Chilean Chemical Society, 2012, vol. 57, # 3, p. 1287 - 1291
[4] Farmaco, 1993, vol. 48, # 5, p. 615 - 636
[5] Gazzetta Chimica Italiana, 1995, vol. 125, # 2, p. 69 - 76