1-Bromoisoquinoline Chemical Properties

Melting point:

42.0 to 46.0 °C

Boiling point:

316.3±15.0 °C(Predicted)

Density 

1.564±0.06 g/cm3(Predicted)

storage temp. 

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

form 

Low Melting Solid

pka

2.03±0.30(Predicted)

color 

Light yellow to light brown

CAS DataBase Reference

1532-71-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

25-41

Safety Statements 

26-45

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

2

HS Code 

29334900

1-Bromoisoquinoline Usage And Synthesis

Chemical Properties

Ligt yellow to light brown low melting solid

Synthesis

General method: To a stirred solution of isoquinoline-N-oxide (0.1 M in anhydrous CH2Cl2), POBr3 (1.2 eq.) was slowly added under argon protection at 0 °C, followed by dropwise addition of DMF (0.5 eq.). The reaction mixture was gradually warmed to 25 °C and stirred continuously until the reaction was complete (monitored by TLC). Upon completion of the reaction, saturated aqueous sodium carbonate solution was slowly added and the pH was adjusted to 7-8. The organic and aqueous phases were separated and the aqueous phase was fully extracted with CH2Cl2. All organic phases were combined, washed with brine, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure to obtain the crude product. The crude product was purified by fast column chromatography with the eluent of petroleum ether/ethyl acetate (100:1).

References

[1] Organic Letters, 2015, vol. 17, # 12, p. 2948 - 2951
[2] Organic Letters, 2013, vol. 15, # 4, p. 792 - 795
[3] Tetrahedron, 2016, vol. 72, # 38, p. 5762 - 5768
[4] Organic Letters, 2016, vol. 18, # 9, p. 1956 - 1959

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