| Identification | Back Directory | [Name]
4-BROMO-1(2H)-ISOQUINOLONE | [CAS]
3951-95-9 | [Synonyms]
4-bromoisocarbostyril
4-Bromoisoquinolin-1-ol
4-BROMO-1(2H)-ISOQUINOLONE
4-broMoisoquinolin-1(2H)-one
4-Bromo-1(2H)-isoquinolinone
4-BROMO-2H-ISOQUINOLIN-1-ONE
4-BROMO-1-HYDROXYISOQUINOLINE
1(2H)-Isoquinolinone, 4-bromo-
4-bromo-1,2-dihydroisoquinolin-1-one
4-BROMO-1(2H)-ISOQUINOLONE ISO 9001：2015 REACH
4-Bromoisoquinolin-1-ol, 4-Bromoisoquinolin-1(2H)-one | [EINECS(EC#)]
622-004-7 | [Molecular Formula]
C9H6BrNO | [MDL Number]
MFCD08437036 | [MOL File]
3951-95-9.mol | [Molecular Weight]
224.05 |
| Chemical Properties | Back Directory | [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 | [InChI]
1S/C9H6BrNO/c10-8-5-11-9(12)7-4-2-1-3-6(7)8/h1-5H,(H,11,12) | [InChIKey]
ZOPUFLIYIMVOGZ-UHFFFAOYSA-N | [SMILES]
BrC1=CNC(=O)c2ccccc12 |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36 | [Safety Statements ]
26 | [WGK Germany ]
3 | [HS Code ]
2933499090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2 |
| Hazard Information | Back Directory | [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 |
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