1-BROMOMETHYL-ISOQUINOLINE Chemical Properties

Melting point:

56℃

Boiling point:

322.1±17.0 °C(Predicted)

Density 

1.518

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

3.90±0.30(Predicted)

Appearance

Pale purple to purple Solid

1-BROMOMETHYL-ISOQUINOLINE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 1-(bromomethyl)isoquinoline from 1-methylisoquinoline is as follows: 1. 1-methylisoquinoline (0.99 g, 6.91 mmol), N-bromosuccinimide (NBS, 1.35 g, 1.1 eq.), azobisisobutyronitrile (AIBN, 10 mg, catalytic amount), and carbon tetrachloride (CCl4, 1 mL) were added to a reaction flask. 2. The reaction mixture was heated to reflux for 2 hours. 3. Upon completion of the reaction, the suspended solid particles were removed by filtration and the solids were washed with a small amount of CCl4. 4. The filtrate and washings were combined and concentrated under reduced pressure to remove the solvent. 5. The crude product was purified by column chromatography (eluent: 30% ethyl acetate/hexane) to afford 1-(bromomethyl)isoquinoline (270 mg, yield: 18%) as a violet solid. 6. The structure of the product was determined by 1H-1H-quinolysis. 6. The structure of the product was confirmed by 1H-NMR (500 MHz, CDCl3): δ 8.48 (d, 1H), 8.25 (d, 1H), 7.87 (d, 1H), 7.75-7.67 (m, 2H), 7.65 (d, 1H).

References

[1] Patent: WO2008/16239, 2008, A1. Location in patent: Page/Page column 57-58

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