5-Hydroxyisoquinoline Chemical Properties

Melting point:

213-215

Boiling point:

264.27°C (rough estimate)

Density 

1.1555 (rough estimate)

refractive index 

1.4500 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

8.53±0.40(Predicted)

form 

Granular Powder

color 

Beige

InChI

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

InChIKey

CSNXUYRHPXGSJD-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

2439-04-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-21/22

Safety Statements 

26-37/39-36/37/39-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29334900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Hydroxyisoquinoline Usage And Synthesis

Chemical Properties

beige granular powder

Uses

5-Hydroxyisoquinoline is a reagent used in the preparation of PARP inhibitor.

Synthesis

The general procedure for the synthesis of 5-hydroxyisoquinoline from 5-isoquinolinesulfonic acid is as follows: 23 g of 5-isoquinolinesulfonic acid is added to 400 ml of water, followed by 60 g of sodium hydroxide. The reaction mixture was heated to reflux and stirred continuously under this condition for 24 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted with dilute hydrochloric acid to 5. Then, ethyl acetate was added for extraction and the organic phase was separated and collected. The organic phase was concentrated and the resulting residue was purified by silica gel column chromatography to yield 16 g of 5-hydroxyisoquinoline.

References

[1] Acta Poloniae Pharmaceutica, 1994, vol. 51, # 6, p. 479 - 482
[2] Patent: CN107778231, 2018, A. Location in patent: Paragraph 0023; 0024

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