Isoquinolin-6-ol Chemical Properties

Melting point:

220 °C

Boiling point:

332.1±15.0 °C(Predicted)

Density 

1.260±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

solid

pka

9.15±0.10(Predicted)

color 

Pale yellow

InChI

InChI=1S/C9H7NO/c11-9-2-1-8-6-10-4-3-7(8)5-9/h1-6,11H

InChIKey

GPVPDRHTRGTSIH-UHFFFAOYSA-N

SMILES

C1C2=C(C=C(O)C=C2)C=CN=1

CAS DataBase Reference

7651-82-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2933499090

Isoquinolin-6-ol Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

6-Hydroxyisoquinoline is used in proteomics research such as in preparation of isoquinoline derivatives which act as protease inhibitors against trypsin. It was also used as a reagent in the study of a novel series of compounds that act as Wnt signaling pathway inhibitors and obtained by scaffold hybridization strategy from two known porcupine inhibitor classes.

Synthesis

(c) 6-Methoxyisoquinoline (16 g, 0.1 mol) was mixed with 48% aqueous hydrobromic acid (600 mL) and heated to reflux for 6 hours. After completion of the reaction, the mixture was concentrated to dryness under reduced pressure. The residue was dissolved in water (H2O) and the pH was adjusted to alkaline with solid sodium carbonate (Na2CO3). The precipitated solid product was collected by filtration and recrystallized with isopropanol to give the final 6-hydroxyisoquinoline (12 g, 82% yield) with a melting point of 205°C. Literature reports a melting point of 218°-220°C (Lit.* 220°C).

References

[1] Patent: US4812573, 1989, A
[2] Patent: WO2004/43904, 2004, A1. Location in patent: Page 59
[3] Patent: WO2004/43931, 2004, A1. Location in patent: Page 36-37
[4] Journal of the American Chemical Society, 1947, vol. 69, p. 1944
[5] European Journal of Organic Chemistry, 2003, # 9, p. 1681 - 1686

Isoquinolin-6-ol(7651-82-3)Related Product Information

• 4-Hydroxybenzoic acid
• 4-Methoxyphenol
• 1,2,3,4-TETRAHYDROISOQUINOLINE
• 10-Hydroxycamptothecin
• Hydroxy silicone oil
• Isoquinoline
• Glycolic acid
• Hydroxyapatite
• 6-Quinazolinol (6CI,7CI,8CI,9CI)
• 6-hydroxyquinoline-3-carboxylic acid
• 6-Hydroxyquinoxaline
• 6-Hydroxyindazole
• 6-Hydroxyindole
• 6-Oxo-3H-pyrimidine-4-carboxylic acid
• Isoquinolin-3-ol
• Nitidine chloride
• PAPAVERINE
• moxaverine