4-(4-Pyridinyl)thiazole-2-thiol Chemical Properties

Boiling point:

364.8±52.0 °C(Predicted)

Density 

1.45±0.1 g/cm3(Predicted)

storage temp. 

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

pka

7.01±0.40(Predicted)

Appearance

Yellow to brown Solid

InChI

InChI=1S/C8H6N2S2/c11-8-10-7(5-12-8)6-1-3-9-4-2-6/h1-5H,(H,10,11)

InChIKey

LEQNUYXXLYRUNY-UHFFFAOYSA-N

SMILES

S1C=C(C2C=CN=CC=2)NC1=S

4-(4-Pyridinyl)thiazole-2-thiol Usage And Synthesis

Chemical Properties

Pale yellow powder

Uses

4-(4-Pyridinyl)thiazole-2-thiol is a reactant used to synthesize novel thiazolidine derivatives and azetidinone derivatives, which possess antiproliferative activity and inhibitory activity against the proliferation of the MCF-7 breast cancer cell line.

Synthesis

The general procedure for the synthesis of 2-mercapto-4-(4-pyridinyl)thiazole from 2-bromo-1-(pyridin-4-yl)ethanone and ammonium dithiocarbamate was as follows: to 1000 ml of water, 60 g of 4-acetylpyridine was added, the temperature was maintained at 10-15 °C, followed by the slow addition of 101 g of hydrobromic acid. Gradually 87.9 g of bromine was added dropwise at the same temperature and the reaction was kept for 1 hour after the dropwise addition. The reaction system was then warmed up to 30-35 °C and the reaction was continued for 4 h. The progress of the reaction was monitored by HPLC until the feedstock was completely consumed. Upon completion of the reaction, the reaction solution was cooled to 0 °C, 66 g of ammonium dithiocarbamate was added and the reaction was kept at 0 °C for 1 hour. After that, the reaction system was slowly warmed up to 20-25°C and the reaction was continued for 4 hours. At the end of the reaction, the solid was collected by filtration to give 81.7 g of crude 2-mercapto-4-(pyridin-4-yl)thiazole. The crude product was refluxed in water for 2 h. After cooling and filtration, 80.2 g of purified 2-mercapto-4-(pyridin-4-yl)thiazole was obtained in 82.6% yield, and the product was a light yellow solid with 99.7% HPLC purity.

References

[1] Patent: CN104031040, 2016, B. Location in patent: Paragraph 0023; 0024

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