| Identification | Back Directory | [Name]
5-BROMOISOQUINOLIN-1(2H)-ONE | [CAS]
190777-77-6 | [Synonyms]
5-bromoisoquinolin-1-ol
5-Bromoisoquinolin-1(2H)
5-Bromo-2H-isoquinolin-1-one
5-BROMOISOQUINOLIN-1(2H)-ONE
5-Bromo-1(2H)-isoquinolinone
1(2H)-Isoquinolinone, 5-bromo-
5-bromanyl-2H-isoquinolin-1-one
5-bromo-1,2-dihydroisoquinolin-1-one
5-Bromo-1,2-dihydro-1-oxoisoquinoline | [Molecular Formula]
C9H6BrNO | [MDL Number]
MFCD11226915 | [MOL File]
190777-77-6.mol | [Molecular Weight]
224.05 |
| Chemical Properties | Back Directory | [Boiling point ]
443.2±45.0 °C(Predicted) | [density ]
1.620 | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
solid | [pka]
12.19±0.20(Predicted) | [color ]
Light yellow to light brown | [InChI]
InChI=1S/C9H6BrNO/c10-8-3-1-2-7-6(8)4-5-11-9(7)12/h1-5H,(H,11,12) | [InChIKey]
UKIWLFJYNMJPEG-UHFFFAOYSA-N | [SMILES]
C1(=O)C2=C(C(Br)=CC=C2)C=CN1 |
| Hazard Information | Back Directory | [Synthesis]
5-Bromo-3,4-dihydroisoquinolin-1(2H)-one (4.3 g, 18.9 mmol) and 2,3-dicyano-5,6-dichloro-1,4-benzoquinone (8.6 g, 37.9 mmol) were mixed in 1,4-dioxane (76 mL). The reaction mixture was stirred at 100 °C for 24 hours. Upon completion of the reaction, the solvent was removed by evaporation and the residue was dissolved in ethyl acetate (500 mL) and washed with 10% aqueous sodium hydroxide solution (2 x 500 mL). The organic and aqueous layers were separated and the aqueous layer was further extracted with ethyl acetate (4 x 300 mL). All organic layers were combined and dried with anhydrous sodium sulfate, then concentrated by evaporation. The product was purified by fast chromatography with the eluent being a solvent mixture of dichloromethane and methanol (ratio tapered from 99:1 to 96:4) to afford 5-bromoisoquinolin-1(2H)-one (1.49 g, 6.65 mmol, 35% yield) as a yellow solid. The product was analyzed by LCMS showing a purity of 94% with a retention time (Rt) of 1.243 min, and electrospray mass spectrometry (ESMS) showed a molecular ion peak m/z of 224 ([M+H]+). | [References]
[1] Patent: WO2014/153055, 2014, A2. Location in patent: Paragraph 0120-0121
[2] Patent: WO2015/20553, 2015, A1. Location in patent: Paragraph 00113-00114
[3] Patent: WO2015/50471, 2015, A1. Location in patent: Paragraph 00107; 00108
[4] Patent: WO2015/50472, 2015, A1. Location in patent: Paragraph 00111; 00112 |
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