10-Hydroxybenzo[h]quinoline

10-Hydroxybenzo[h]quinoline Property

Melting point:

103-105°C

Boiling point:

420.6±18.0 °C(Predicted)

Density 

1.307±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in acetone, chloroform and ethyl acetate.

form 

Solid

pka

8.03±0.30(Predicted)

color 

Yellow

BRN 

141770

InChI

InChI=1S/C13H9NO/c15-11-5-1-3-9-6-7-10-4-2-8-14-13(10)12(9)11/h1-8,15H

InChIKey

KESRRRLHHXXBRW-UHFFFAOYSA-N

SMILES

N1C2C(=CC=C3C=CC=C(O)C3=2)C=CC=1

CAS DataBase Reference

33155-90-7(CAS DataBase Reference)

Safety

Risk Statements 

36/37/38

Safety Statements 

26-37

HS Code 

29334900

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.

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

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P405Store locked up.

10-Hydroxybenzo[h]quinoline Chemical Properties,Usage,Production

Chemical Properties

Light yellow solid

Uses

5-Hydroxy-4-azaphenanthrene is used to detect boronic acids in reactions and boron containing compounds on solid support. 5-Hydroxy-4-azaphenanthrene is also used as a proton transfer-fluoresence probe to be applied to human serum albumin and beaver apomyoglobin.

Synthesis

10-Bromobenzo[h]quinoline (0.15 mmol, 39 mg) was added to an oven-dried screw-capped vial with carboxylic acid (0.3 mmol), silver carbonate (Ag-based, 0.165 mmol, 22 mg), potassium fluoride (0.15 mmol, 9 mg) and p-xylene (0.5 mL). The reaction mixture was stirred vigorously at 150 °C for 24 hours. After completion of the reaction, the mixture was cooled to room temperature and diluted with ethyl acetate. Subsequently, the solvent was removed by distillation under reduced pressure and the final product was purified by silica gel column chromatography.

References

[1] Tetrahedron Letters, 2016, vol. 57, # 7, p. 781 - 783
[2] Tetrahedron Letters, 2016, vol. 57, # 7, p. 781 - 783