1H-Isoindol-1-one, 2,3-dihydro-6-hydroxy- (9CI) Chemical Properties

Boiling point:

507.3±50.0 °C(Predicted)

Density 

1.362±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

9.43±0.20(Predicted)

form 

solid

color 

Off-white

Safety Information

HS Code 

2933998090

1H-Isoindol-1-one, 2,3-dihydro-6-hydroxy- (9CI) Usage And Synthesis

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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