Identification | Back Directory | [Name]
1H-Isoindol-1-one, 2,3-dihydro-6-hydroxy- (9CI) | [CAS]
659737-57-2 | [Synonyms]
6-hydroxyisoindolin-1-one 6-hydroxy-1-isoindolinone 6-Hydroxy-2,3-dihydro-1H-isoindol-1-one 1H-Isoindol-1-one, 2,3-dihydro-6-hydroxy- 1H-Isoindol-1-one, 2,3-dihydro-6-hydroxy- (9CI) | [Molecular Formula]
C8H7NO2 | [MDL Number]
MFCD08276013 | [MOL File]
659737-57-2.mol | [Molecular Weight]
149.15 |
Chemical Properties | Back Directory | [Boiling point ]
507.3±50.0 °C(Predicted) | [density ]
1.362±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [form ]
solid | [pka]
9.43±0.20(Predicted) | [color ]
Off-white |
Hazard Information | Back Directory | [Synthesis]
5-Methoxy-2,3-dihydroisoindol-1-one (167 mg, 1.0 mmol) was used as a starting material, which was dissolved in dichloromethane (8 mL) and cooled to -78°C. Subsequently, boron tribromide (1 M in dichloromethane, 3.6 mL, 3.6 mmol) was added. The reaction mixture was slowly warmed to room temperature and stirred for 18 hours. After the reaction was complete, the mixture was cooled again to -78 °C and methanol (20 mL) was slowly added. After continued stirring at -78 °C for 2 h, the solvent was removed by evaporation. The residue was purified by silica gel column chromatography with the eluent being dichloromethane:2N ammonia methanol solution (9:1) to afford the target product 6-hydroxy-isoindolin-1-one (147 mg, 100% yield) as a white solid. Mass spectrometry analysis showed m/e = 148.0 (M-H+). | [References]
[1] Patent: WO2004/14856, 2004, A1. Location in patent: Page 10; 23 [2] Patent: WO2008/20306, 2008, A2. Location in patent: Page/Page column 26; 28 [3] Tetrahedron Letters, 2009, vol. 50, # 12, p. 1267 - 1269 [4] Patent: WO2008/20306, 2008, A2. Location in patent: Page/Page column 26; 28 [5] Patent: WO2006/138549, 2006, A1. Location in patent: Page/Page column 73 |
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