4-BROMO-1(2H)-ISOQUINOLONE Chemical Properties

Melting point:

248-249 °C (decomp)(Solv: acetic acid (64-19-7); water (7732-18-5))

Boiling point:

408.0±45.0 °C(Predicted)

Density 

1.666±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

11.91±0.40(Predicted)

Appearance

White to light brown Solid

InChIKey

ZOPUFLIYIMVOGZ-UHFFFAOYSA-N

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

WGK Germany 

3

HS Code 

2933499090

4-BROMO-1(2H)-ISOQUINOLONE Usage And Synthesis

Synthesis

General procedure for the synthesis of 4-bromo-1(2H)-isoquinolinone from 1-hydroxyisoquinoline: N-bromosuccinimide (NBS, 142 mg, 0.796 mmol) was added to a solution of DMF (2 mL) containing isoquinolin-1(2H)-one (105 mg, 0.723 mmol). The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the mixture was concentrated to remove the solvent. The crude product was purified by preparative high performance liquid chromatography (HPLC) to afford the intermediate 6 4-bromoisoquinolin-1(2H)-one (110 mg, 68% yield). [C] MS (ESI) m/z: 223.9 (M + H)+. 1H NMR (500 MHz, DMSO-d6) δ 11.57 (br.s, 1H), 8.24 (dd, J = 8.0, 0.8 Hz, 1H), 7.88-7.83 (m, 1H), 7.79-7.75 (m, 1H), 7.61 (ddd, J = 8.0, 7.1, 1.1 Hz, 1H), 7.55 (s, 1H).

References

[1] Journal of Medicinal Chemistry, 2014, vol. 57, # 4, p. 1299 - 1322
[2] Angewandte Chemie - International Edition, 2011, vol. 50, # 36, p. 8416 - 8419
[3] Synthetic Communications, 2007, vol. 37, # 23, p. 4199 - 4208
[4] Patent: US2014/206686, 2014, A1. Location in patent: Paragraph 0497-0499
[5] Patent: WO2016/69976, 2016, A1. Location in patent: Page/Page column 91

4-BROMO-1(2H)-ISOQUINOLONE(3951-95-9)Related Product Information

• 4-broMo-2-(trifluoroMethyl)pyriMidine
• 4-BROMO-6,7-DIMETHOXYQUINOLINE
• 4-bromo-1,5-dimethyl-1H-pyrazole
• 3-(4-BROMO-PYRAZOL-1-YLMETHYL)-PYRIDINE
• 7-BROMO-1(2H)-ISOQUINOLONE
• 4-bromo-2-methyl-isoquinolin-1-one
• Isocarbostyril
• 2-Hydroxy-5-bromopyridine
• 4-Bromoisoquinoline
• 4-BROMO-1-METHOXYISOQUINOLINE
• 4-BROMO-1(2H)-ISOQUINOLONE