7-BROMO-1-HYDROXYISOQUINOLINE Chemical Properties

Melting point:

248-250°C

Boiling point:

427.5±45.0 °C(Predicted)

Density 

1.620±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

Inert atmosphere,Room Temperature

form 

solid

pka

12.34±0.20(Predicted)

color 

Off-white to light yellow

Water Solubility 

Slightly soluble in water.

BRN 

8405244

InChI

InChI=1S/C9H6BrNO/c10-7-2-1-6-3-4-11-9(12)8(6)5-7/h1-5H,(H,11,12)

InChIKey

DSOKREQUHLPVFR-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=CC(Br)=C2)C=CN1

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-41-37/38-22

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2933499090

MSDS

• Language:English Provider:ALFA

7-BROMO-1-HYDROXYISOQUINOLINE Usage And Synthesis

Uses

7-Bromo-1-hydroxyisoquinoline acts as a pharmaceutical intermediate. It is also used to prepare 1-amino-4-bromoisoquinoline.

Synthesis

7-Bromo-1-chloroisoquinoline (1a, 2.70 g, 11.10 mmol) was used as starting material, which was dissolved in acetic acid (50 mL), followed by the addition of ammonium acetate (1b, 8.50 g, 111.10 mmol). The reaction mixture was placed in an oil bath at 100 °C and the reaction was stirred for 4 hours. After completion of the reaction, the reaction mixture was concentrated to dryness by rotary evaporator. An appropriate amount of water was added to the residue and a white solid precipitated. The solid product was collected by filtration and washed with water to afford 7-bromoisoquinolin-1(2H)-one (1c, 2.7 g, white solid). The crude product was used directly in the subsequent reaction without further purification. Mass spectrum (ESI) m/z: 225.9 [M + 1]+. 1H NMR (400 MHz, CDCl3) δ: 8.55 (d, J = 1.8 Hz, 1H), 7.75 (dd, J = 2.1, 8.5 Hz, 1H), 7.43 (d, J = 8.6 Hz, 1H), 7.14 (d, J = 6.2 Hz, 1H), 6.52 ( d, J = 7.3 Hz, 1H).

References

[1] Chemical Communications, 2018, vol. 54, # 75, p. 10574 - 10577
[2] Patent: EP3042907, 2016, A1. Location in patent: Paragraph 0324; 0325

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