| Identification | Back Directory | [Name]
8-BROMO-2H-ISOQUINOLIN-1-ONE | [CAS]
475994-60-6 | [Synonyms]
8-Bromoisoquinolin-1-ol
8-Bromoisoquinolin-1(2H)
8-Bromoisoquinolin-1(2H)-one
8-Bromo-1(2H)-isoquinolinone
8-BROMO-2H-ISOQUINOLIN-1-ONE
8-BroMo-2H-isoquinoline-1-one
8-Bromo-1-hydroxyisoquinoline
1(2H)-Isoquinolinone, 8-bromo-
8-bromo-1(2H)-isoquinolin-1-one | [Molecular Formula]
C9H6BrNO | [MDL Number]
MFCD11858429 | [MOL File]
475994-60-6.mol | [Molecular Weight]
224.05 |
| Chemical Properties | Back Directory | [Boiling point ]
446.1±45.0 °C(Predicted) | [density ]
1.620±0.06 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
2-8°C | [form ]
powder | [pka]
11.81±0.20(Predicted) | [color ]
Yellow | [InChI]
InChI=1S/C9H6BrNO/c10-7-3-1-2-6-4-5-11-9(12)8(6)7/h1-5H,(H,11,12) | [InChIKey]
NQMZAFRCYDJSEU-UHFFFAOYSA-N | [SMILES]
C1(=O)C2=C(C=CC=C2Br)C=CN1 |
| Hazard Information | Back Directory | [Synthesis]
The general procedure for the synthesis of 8-bromoisoquinolin-1(2H)-one from 8-bromoisoquinoline 2-oxide was as follows: 8-bromoisoquinoline 2-oxide (630 mg, 2.8 mmol) was suspended in N,N-dimethylformamide (DMF, 10 mL), and treated with trifluoroacetic anhydride (4 mL). The reaction mixture was stirred overnight at room temperature until the solution was clarified. Subsequently, the reaction solution was concentrated under reduced pressure to remove the solvent. The residue was neutralized with dilute aqueous sodium carbonate and extracted several times with a 5% methanol/dichloromethane mixture. The organic phases were combined, washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography, eluting with a gradient of 0-10% methanol in dichloromethane solution to give a white solid product (180 mg, 29% yield). Mass spectrometric analysis (positive ion electrospray mode) showed m/z 225 [M+H]+. | [References]
[1] Patent: WO2004/2992, 2004, A1. Location in patent: Page 76; 77
[2] Tetrahedron, 2002, vol. 58, # 29, p. 5761 - 5766
[3] Patent: WO2017/100591, 2017, A1. Location in patent: Paragraph 00226 |
|
|