2,1,3-Benzothiadiazol-5-ylmethanol Chemical Properties

Melting point:

61-63

Boiling point:

313.5±17.0 °C(Predicted)

Density 

1.466±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

13.59±0.10(Predicted)

Appearance

White to off-white Solid

CAS DataBase Reference

89795-51-7

Safety Information

Safety Statements 

24/25

2,1,3-Benzothiadiazol-5-ylmethanol Usage And Synthesis

Synthesis

General procedure for the synthesis of 2,1,3-benzothiadiazole-5-methanol from 2,1,3-benzothiadiazole-5-carboxylic acid: 2,1,3-benzothiadiazole-5-carboxylic acid (2.00 g, 11.11 mmol) was dissolved in tetrahydrofuran (50 mL) and the solution was cooled to 0 °C. Subsequently, triethylamine (1.80 mL, 12.87 mmol) was slowly added dropwise followed by isobutyl chloroformate (1.62 mL, 12.40 mmol). The reaction mixture was continued to be stirred at 0 °C for 30 min and then filtered into a pre-cooled mixture of sodium borohydride (0.83 g, 21.84 mmol) and ice water (20 mL). The reaction system was kept at 0 °C and stirring was continued for 30 min. Subsequently, the reaction solution was concentrated to one-fourth of the original volume and extracted with dichloromethane (3 x 50 mL). The organic phases were combined and dried with anhydrous sodium sulfate. Finally, the organic phase was concentrated under reduced pressure to afford the target product 2,1,3-benzothiadiazole-5-methanol as a white solid in 81% yield (1.50 g), which could be used for subsequent experiments without further purification.

References

[1] Patent: WO2003/87098, 2003, A1. Location in patent: Page/Page column 39
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 21, p. 3378 - 3390

2,1,3-Benzothiadiazol-5-ylmethanol(89795-51-7)Related Product Information

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