Isoquinoline-5-boronic acid Chemical Properties

Melting point:

204-206

Boiling point:

419.1±37.0 °C(Predicted)

Density 

1.28±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

form 

solid

pka

7.70±0.30(Predicted)

color 

Off white to light yellow

InChIKey

XKEYHBLSCGBBGU-UHFFFAOYSA-N

CAS DataBase Reference

371766-08-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

HazardClass 

IRRITANT

HS Code 

2933499090

Isoquinoline-5-boronic acid Usage And Synthesis

Uses

Isoquinoline-5-boronic acid, HCl

Synthesis

To a solution of 5-bromoisoquinoline (1.46 g, 7.0 mmol) in THF (20 mL) prepared according to the literature method (Brown, W. D et al., Synthesis 2002, 83), triisopropyl borate (2.4 mL, 10.5 mmol) and tertiary-butyllithium (1.7 M, 9.5 mL) were sequentially added at -78 °C. The reaction mixture was slowly warmed to room temperature and stirred overnight. Upon completion of the reaction, the reaction was quenched with 1N HCl (10 mL) and a solid product was obtained after decantation of the THF layer. The solid was identified as 5-isoquinolineboronic acid (1.0 g, 82% yield). The mass spectrum (ESI) showed the (M + 1) peak as 174.12.

References

[1] Patent: WO2005/72732, 2005, A1. Location in patent: Page/Page column 61
[2] Patent: WO2008/6480, 2008, A1. Location in patent: Page/Page column 5-6

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