2,1,3-Benzothiadiazol-5-ylmethanol

2,1,3-Benzothiadiazol-5-ylmethanol Property

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

Safety Statements 

24/25

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

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

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