5-FLUORO-2-MERCAPTOBENZOTHIAZOLE Chemical Properties

Melting point:

189-191 °C(Solv: chloroform (67-66-3); ligroine (8032-32-4))

Boiling point:

295.7±42.0 °C(Predicted)

Density 

1.55±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMSO (Slightly), Ethyl Acetate (Slightly)

form 

Solid

pka

8.96±0.20(Predicted)

color 

Pale Brown to Light Brown

Sensitive 

Stench

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant/Stench

HS Code 

2934208090

5-FLUORO-2-MERCAPTOBENZOTHIAZOLE Usage And Synthesis

Chemical Properties

Gray solid

Uses

5-Fluoro-2-mercaptobenzothiazole is used as a reagent in the synthesis of [[(benzothiazolyl)thio]methyl]phenyl]furanone derivatives with agrochemical fungicidal activities.

Synthesis

Step 1) Synthesis of 5-fluorobenzo[d]thiazole-2-thiol: 2,5-difluoroaniline (1.00 g, 7.75 mmol) and potassium ethylxanthate (2.73 g, 17.05 mmol) were dissolved in N,N-dimethylformamide (50 mL). The reaction mixture was heated to 120 °C for 10 hours. After completion of the reaction, the mixture was cooled to room temperature and diluted with deionized water (100 mL). The pH of the mixture was adjusted to 4-5 with 1 M hydrochloric acid, at which point a solid precipitated. The solid was collected by diafiltration and dried at 50 °C. Ultimately, 5-fluoro-2-mercaptobenzothiazole was obtained as a white solid (1.11 g, 76.5% yield) under vacuum. Mass spectrum (ESI, cation mode) m/z: 185.00 [M + H]+; 1H NMR (DMSO-d6, 600 MHz) δ (ppm): 13.98 (s, 1H), 7.55 (d, J = 8.2 Hz, 1H), 7.36-7.31 (m, 2H).

References

[1] Synthetic Communications, 2007, vol. 37, # 3, p. 369 - 376
[2] Patent: WO2017/88759, 2017, A1. Location in patent: Paragraph 00232
[3] Patent: WO2011/143366, 2011, A1. Location in patent: Page/Page column 57
[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7661 - 7670

5-FLUORO-2-MERCAPTOBENZOTHIAZOLE(155559-81-2)Related Product Information

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