3-Thiophenecarbonitrile

Chemical Properties

Clear colorless liquid

Uses

3-Thiophenecarbonitrile can be used to synthesize the following:

• 2,4-dinaphthyl-3-cyanothiophene via reaction with iodonaphthalene
• 2,5-bis-tri(n-butyl)tin-3-cyanothiophene, a building block for the synthesis of new alternating (3-alkyl/3-cyano)thiophene copolymers

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 1670, 1979 DOI: 10.1021/jo01324a019
Synthetic Communications, 20, p. 3153, 1990 DOI: 10.1080/00397919008051539

Synthesis

General procedure for the synthesis of 3-cyanothiophene from 3-thiophenecarboxaldehyde: A mixture of 3-thiophenecarboxaldehyde (1.0 mmol), NH2OH-HCl (1.5 mmol), and Cog-C3N4 (20 mg) in H2O/MeOH (1:1, 5 mL) was added to a round-bottomed flask and the reaction was stirred for 14-20 h at room temperature under visible-light irradiation. The reaction progress was monitored by TLC. After completion of the reaction, the catalyst was removed by filtration and the filtrate was extracted by adding EtOAc (10 mL) to the filtrate. The organic layer was separated and washed sequentially with brine (2 x 5 mL) and distilled water (1 x 10 mL) and then dried with anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give the crude product. The crude product was further purified by fast column chromatography with the eluent ratio of EtOAc/hexane (10:90) to obtain analytically pure 3-cyanothiophene.

References

[1] Organic Letters, 2017, vol. 19, # 11, p. 3005 - 3008
[2] Catalysis Communications, 2019, p. 76 - 81
[3] Journal of Polymer Science, Part A: Polymer Chemistry, 2014, vol. 52, # 8, p. 1055 - 1058
[4] Tetrahedron Letters, 2012, vol. 53, # 7, p. 882 - 885
[5] Chemical Communications, 2013, vol. 49, # 54, p. 6030 - 6032