1H-Isoindol-1-one, 2,3-dihydro-5-hydroxy- (9CI) Chemical Properties

Boiling point:

519.4±50.0 °C(Predicted)

Density 

1.362±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

9.03±0.20(Predicted)

form 

solid

color 

White

Safety Information

HS Code 

2933998090

1H-Isoindol-1-one, 2,3-dihydro-5-hydroxy- (9CI) Usage And Synthesis

Uses

5-Hydroxyisoindolin-1-one, can be used in the synthesis of chemical compounds, such as in design and Synthesis of Pyrrolo[3,2-d]pyrimidine Human Epidermal Growth Factor Receptor.

Synthesis

General procedure for the synthesis of 5-hydroxy-isoindolin-1-one from 5-methoxy-2,3-dihydroisoindol-1-one: To a suspension of 5-methoxy-2,3-dihydroisoindol-1-one (5.65 g, 34.6 mmol) in dichloromethane (300 mL) was added slowly and dropwise over a period of 20 min boron tribromide (25.1 g, 100 mmol, 1.0 M dichloromethane solution). After the dropwise addition, the reaction mixture was gradually warmed to room temperature and stirring was continued for 3 hours. Subsequently, the reaction was quenched with methanol (100 mL) at 0 °C and stirring was continued for 3 hours. Upon completion of the reaction, the reaction solution was concentrated, water (500 mL) was added, heated to 60 °C and kept for 1 hour. After cooling, the solid product 5-hydroxy-2,3-dihydroisoindol-1-one was obtained by filtration (4.10 g, 79% yield, CAS No. 252061-66-8). Mass spectrometry (electrospray ionization): m/z 150.0 [M+H]+ (calculated value: 149.0).

References

[1] Patent: WO2008/20306, 2008, A2. Location in patent: Page/Page column 35-36
[2] Patent: WO2004/14856, 2004, A1. Location in patent: Page 9; 14-15
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 8, p. 3975 - 3991
[4] Journal of Medicinal Chemistry, 1999, vol. 42, # 23, p. 4875 - 4889
[5] Chemical and Pharmaceutical Bulletin, 2011, vol. 59, # 1, p. 96 - 99

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