3-Thiophenecarbonitrile Chemical Properties

Boiling point:

82 °C10 mm Hg(lit.)

Density 

1.2 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.5630(lit.)

Flash point:

186 °F

storage temp. 

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

form 

Liquid

Specific Gravity

1.2

color 

Clear colorless

BRN 

107104

CAS DataBase Reference

1641-09-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36-36/37

RIDADR 

3276

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

6.1

PackingGroup 

III

HS Code 

29341000

MSDS

• Language:English Provider:3-Cyanothiophene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Thiophenecarbonitrile Usage And Synthesis

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

3-Thiophenecarbonitrile(1641-09-4)Related Product Information

• Tetrahydrothiophene
• ETHYL 2-CYANOACRYLATE
• Benzonitrile
• Methylene dithiocyanate
• Cyanoacetic acid
• Thifensulfuron
• Thiophene
• Thifensulfuron methyl
• Poly(3-hexylthiophene-2,5-diyl)
• Cephalothin sodium
• Sodium cyanoborohydride
• 4-Nitrobenzonitrile
• 2-NITROTHIOPHENE-4-CARBONITRILE
• N1-(3-CYANO-4-METHYL-2-THIENYL)-2-CHLOROACETAMIDE
• 2-AMINO-4,5-TRIMETHYLENE-3-THIOPHENECARBONITRILE
• METHYL 3-AMINO-4-CYANOTHIOPHENE-2-CARBOXYLATE
• 2-Thiophenecarbonitrile
• ETHYL 3-AMINO-4-CYANO-5-(METHYLTHIO)THIOPHENE-2-CARBOXYLATE