4-Bromo-1-chloroisoquinoline Chemical Properties

Melting point:

97 °C (decomp)

Boiling point:

328.8±22.0 °C(Predicted)

Density 

1.673±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-0.02±0.31(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C9H5BrClN/c10-8-5-12-9(11)7-4-2-1-3-6(7)8/h1-5H

InChIKey

HRWILRGBDZGABZ-UHFFFAOYSA-N

SMILES

C1(Cl)C2=C(C=CC=C2)C(Br)=CN=1

CAS DataBase Reference

66728-98-1(CAS DataBase Reference)

Safety Information

HS Code 

2933499090

4-Bromo-1-chloroisoquinoline Usage And Synthesis

Uses

4-Bromo-1-chloroisoquinoline is an isoquinoline derivative whose molecular structure contains substituents chlorine and bromine atoms at positions 1 and 4. The product can be used in metal-catalysed cross-coupling reactions and in the preparation of pharmaceuticals.

Synthesis

The general procedure for the synthesis of 4-bromo-1-chloroisoquinolines from 4-bromo-1(2H)-isoquinolinones was as follows: 4-bromoisoquinolin-1-ol (1.4 g, 5.80 mmol) was mixed with phosphorus trichloride (POCl3, 8.9 g, 58.09 mmol, 10 equiv.) and heated to reflux under stirring conditions. The progress of the reaction was monitored by liquid chromatography-mass spectrometry (LCMS) and it was confirmed that the reaction was completed after 4 hours. The reaction mixture was cooled to room temperature and the reaction was quenched with ice water (100 mL) followed by extraction with ethyl acetate (EtOAc, 3 x 25 mL). The organic phases were combined and washed sequentially with water (3 × 20 mL), saturated aqueous sodium bicarbonate (30 mL) and brine (20 mL). The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent to afford 4-bromo-1-chloroisoquinoline as a white solid 1.3 g in 87% yield.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222

4-Bromo-1-chloroisoquinoline(66728-98-1)Related Product Information

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• Isoquinoline
• CHLORODIBROMOMETHANE
• 1-Chloroisoquinoline
• Chlorobromoisocyanurate
• 4-bromo-1-cyclopropyl-1H-pyrazole
• methyl 4-bromo-1-methyl-1H-pyrazole-5-carboxylate
• 4-BroMo-1-cyclopentylpyrazole
• 4-Bromoisoquinoline
• 5-Bromo-2-chloropyridine
• Bromine
• 7-BROMO-1-CHLOROISOQUINOLINE
• 6-Bromo-1-chloroisoquinoline
• 5-BROMO-1-CHLOROISOQUINOLINE
• 1-BROMO-4-CHLOROISOQUINOLINE
• 6-BROMO-3-CHLOROISOQUINOLINE
• 5-BROMO-8-CHLOROISOQUINOLINE
• 4-Bromo-1-chloroisoquinoline