1,2,3-BENZOTHIADIAZOLE Chemical Properties

Melting point:

295 °C (decomp)

Boiling point:

220.5±23.0 °C(Predicted)

Density 

1.368±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

-2.83±0.50(Predicted)

Appearance

Light yellow to yellow Solid

1,2,3-BENZOTHIADIAZOLE Usage And Synthesis

Synthesis

The general procedure for the synthesis of benzo[d][1,2,3]thiadiazole from 2-aminothiophenol was as follows: o-aminothiophenol (0.3 mmol, 1 eq.) and tert-butyl nitrite (0.45 mmol, 1.5 eq.) were sequentially added to the reaction vessel at room temperature (25 °C), followed by the addition of 2 mL of water as reaction solvent. The reaction mixture was stirred at 25 °C for 3 min. After the reaction was completed, 10 mL of ethyl acetate was added to dilute the reaction solution, and the diluted solution was transferred to a partition funnel and extracted with saturated saline to separate the aqueous and organic phases. The aqueous phase was then extracted with ethyl acetate 2 to 4 times. All organic phases were combined and dried with 5 g of anhydrous sodium sulfate for 5 min, followed by filtration. The filter cake was washed with ethyl acetate (5 mL x 3 times) and then concentrated under reduced pressure. Finally, the concentrate was separated by column chromatography (eluent was petroleum ether to ethyl acetate 3:1 by volume) and the eluate was collected. After removing the solvent, a white liquid product was obtained in 96% yield.

Purification Methods

1,2,3-Benzothiadiazole crystallises from pet ether, and has at 264 and 306nm in hexane. [Overberger et al. J Org max Soc 24 1407 1959, Beilstein 27 III/IV 7113.]

References

[1] Synthesis, 2011, # 13, p. 2154 - 2158
[2] Patent: CN107311960, 2017, A. Location in patent: Paragraph 0044-0047; 0144-0147
[3] Patent: WO2011/100502, 2011, A1. Location in patent: Page/Page column 48-49
[4] Phosphorus and Sulfur and the Related Elements, 1984, vol. 19, p. 279 - 284
[5] Justus Liebigs Annalen der Chemie, 1893, vol. 277, p. 227,228

1,2,3-BENZOTHIADIAZOLE(273-77-8)Related Product Information

• 5-Benzothiazolecarboxylicacid,methylester(9CI)
• methyl 1,3-benzodioxole-5-carboxylate
• 1,2,3-Benzothiadiazole-5-carboxaldehyde
• 1,2,3-BENZOTHIADIAZOLE-5-CARBOXYLIC ACID
• ACIBENZOLAR-S-METHYL
• 1,2,3-Benzothiadiazole-5-carbonyl chloride (9CI)
• 1,2,3-Benzothiadiazole-4-carboxylicacid
• 5-Chloro-4-Amino-1,2,3-Benzothiadiazole
• 2,1,3-Benzothiadiazole-4-sulphonyl chloride
• 5-Amino-2,1,3-benzothiadiazole
• 1,2,3-Benzothiadiazole-5-sulfonylchloride
• 2,1,3-Benzothiadiazole-5-carbonyl chloride (9CI)
• 5-(Bromomethyl)-2,1,3-benzothiadiazole, 95+%
• 4-ISOCYANATO-2,1,3-BENZOTHIADIAZOLE
• 5-CHLORO-N-(4,5-DIHYDR-1H-IMIDAZOL-2-YL)-2,1,3-BENZOTHIADIAZOLE-4-AMINE
• METHYL 1,2,3-BENZOTHIADIAZOLE-5-CARBOXYLATE
• 1,2,3-Benzothiadiazole-6-carboxylic acid methyl ester
• 5-(BROMOMETHYL)-1,2,3-BENZOTHIADIAZOLE