3-Thiophenecarbonitrile, 5-chloro- Chemical Properties

Boiling point:

203.2±20.0 °C(Predicted)

Density 

1.42±0.1 g/cm3(Predicted)

storage temp. 

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

Appearance

Light brown to brown Solid-liquid mixture

3-Thiophenecarbonitrile, 5-chloro- Usage And Synthesis

Synthesis

General procedure for the synthesis of 5-chloro-3-thiophenecarbonitrile from 3-cyanothiophene: Preparation of Intermediate 1M Synthesis: In a 100 mL three-necked round-bottomed flask, 3-cyanothiophene (5.0 g, 1 eq.) was dissolved in acetic acid (50 mL, 10 v/v), followed by N-chlorosuccinimide (6.73 g, 1.1 eq.). The reaction mixture was stirred at reflux temperature for 2-3 hours. The reaction progress was monitored by thin layer chromatography (TLC) using ethyl acetate: hexane (1:9) as mobile phase. Upon completion of the reaction, the mixture was cooled to room temperature and poured into an ice-water slurry (250 mL) and neutralized with sodium bicarbonate solution. The product was extracted with ethyl acetate (100 mL x 3). The organic layer was washed sequentially with brine solution (100 mL x 2) and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to give 5.0 g of crude product. Purification by fast column chromatography using ethyl acetate and hexane as eluents gave 2.4 g of pure product in 36.5% yield. MS/LCMS: m/z 177.0. nuclear magnetic resonance spectroscopy (NMR) confirmed the structure.

References

[1] Patent: WO2011/109799, 2011, A1. Location in patent: Page/Page column 145

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