3-Cyanomethylthiophene Chemical Properties

Boiling point:

124-125 °C/16 mmHg (lit.)

Density 

1.08 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.545(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Light yellow to Light orange

Specific Gravity

1.080

BRN 

107774

CAS DataBase Reference

13781-53-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,T

Risk Statements 

20/21/22-36/37/38-23/24/25

Safety Statements 

26-36/37-45-36/37/39

RIDADR 

UN 3276 6.1/PG 2

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

29349990

MSDS

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

3-Cyanomethylthiophene Usage And Synthesis

Chemical Properties

clear yellow to brown liquid

Uses

3-Thiopheneacetonitrile was used in the synthesis of:

• (E)-3-phenyl-2-(3-thienyl) acrylonitrile
• (Z)-3-(4-methylphenyl)-2-(3-thienyl) acrylonitrile

Synthesis

General procedure for the synthesis of 3-thiophene acetonitrile from 3-methylthiophene and trimethylcyanosilane: N-bromosuccinimide (NBS, 9.07 g, 50.9 mmol, 1 eq.) and azobisisobutyronitrile (AIBN, 836 mg, 5.1 mmol, 0.1 eq.) were added to 3-methylthiophene (5 g, 50.9 mmol, 1 eq.) in carbon tetrachloride ( CCl4, 20 mL) solution. The reaction mixture was refluxed for 1 hour. After completion of the reaction, it was cooled to room temperature and the solvent was removed by evaporation under reduced pressure. The residue was dissolved in anhydrous acetonitrile (40 mL). Trimethylcyanosilane (TMSCN, 20 mL, 153 mmol, 3 eq.) and tetrabutylammonium fluoride (TBAF, 1 M solution of THF, 153 mL, 153 mmol, 3 eq.) were added slowly and dropwise to the solution at 0 °C and under argon protection. The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the solvent was removed by evaporation under reduced pressure. The residue was purified by fast column chromatography (eluent: 5% ethyl acetate/cyclohexane) to afford the orange oily product 3-thiophene acetonitrile (4.06 g, 33 mmol, 65% overall yield in two steps). The product was characterized as follows: 1H NMR (300 MHz, CDCl3): δ 7.22 (dd, J = 5.0, 3.0 Hz, 1H), 7.10 (dd, J = 2.8, 1.1 Hz, 1H), 6.90 (dd, J = 5.0, 1.2 Hz, 1H), 3.58 (s, 2H) ppm; 13C NMR (100 MHz CDCl3): δ 129.4, 127.0, 126.9, 122.9, 117.7, 18.4 ppm; IR (neat): ν 3104, 2360, 2340, 2255, 1688, 1415, 832, 771, 692 cm-1; GC-MS: m/z C6H5NS [M+] 122.

References

[1] Tetrahedron, 2013, vol. 69, # 22, p. 4473 - 4478

3-Cyanomethylthiophene(13781-53-8)Related Product Information

• BENZO[B]THIOPHENE-3-ACETONITRILE
• 5-CHLOROTHIANAPHTHENE-3-ACETONITRILE
• 3-Cyanomethylthiophene
• CIS-1,2-DICYANO-1,2-BIS(2,4,5-TRIMETHYL-3-THIENYL)ETHENE
• 2-Cyanomethylthiophene
• 3-(3,4-DIMETHYLANILINO)-2-(3-THIENYL)ACRYLONITRILE
• 3-(DIMETHYLAMINO)-2-(3-THIENYL)ACRYLONITRILE
• 3-(CYANOMETHYL)-2,4,5-TRIMETHYLTHIOPHENE
• (5-METHYL-1-BENZOTHIEN-3-YL)ACETONITRILE
• 3-[3-(METHYLSULFANYL)ANILINO]-2-(3-THIENYL)ACRYLONITRILE
• 4-([2-CYANO-2-(3-THIENYL)VINYL]AMINO)BENZENECARBOXYLIC ACID
• 3-(4-PHENOXYANILINO)-2-(3-THIENYL)ACRYLONITRILE
• 2-(3-THIENYL)-3-(4-TOLUIDINO)ACRYLONITRILE
• 3-(DIMETHYLAMINO)-2-(3-THIENYL)ACRYLONITRILE
• 3-(2,4-DIMETHOXYANILINO)-2-(3-THIENYL)ACRYLONITRILE
• 3-(2,4-DICHLOROANILINO)-2-(3-THIENYL)ACRYLONITRILE
• METHYL 4-([2-CYANO-2-(3-THIENYL)VINYL]AMINO)BENZENECARBOXYLATE
• 3-ANILINO-2-(3-THIENYL)ACRYLONITRILE