2-(1-PHENYLETHYLIDENE)MALONONITRILE Chemical Properties

Melting point:

94-96°C

Boiling point:

165 °C(Press: 12 Torr)

Density 

1.096±0.06 g/cm3(Predicted)

storage temp. 

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

Appearance

Off-white to light yellow Solid

EPA Substance Registry System

Propanedinitrile, (1-phenylethylidene)- (5447-87-0)

Safety Information

HazardClass 

IRRITANT

HS Code 

2926907090

2-(1-PHENYLETHYLIDENE)MALONONITRILE Usage And Synthesis

Synthesis Reference(s)

Tetrahedron Letters, 4, p. 955, 1963 DOI: 10.1039/jr9630005127

Synthesis

Malononitrile (32 mmol) and acetophenone (28 mmol) were dissolved in 20 mL of toluene solution containing ammonium acetate (500 mg, 6.5 mmol) and glacial acetic acid (2 mL) in a 50 mL round bottom flask. The water generated during the reaction was removed by vigorous reflux using a Dean-Stark water separator mounted under the reflux condenser. Upon completion of the reaction, the toluene was removed by evaporation to give the crude product. The crude product was further purified by recrystallization from ethanol or vacuum distillation to afford the target compound 2-(1-phenylethylidene)malononitrile in 61% yield. The structure of the product was confirmed by 1H NMR (CDCl3, 300 MHz) and 13C NMR (CDCl3, 75 MHz): 1H NMR δ 7.56-7.50 (m, 5H, ArH), 2.63 (s, 3H); 13C NMR δ 175.4, 135.7, 132.1, 128.9, 127.2, 112.7, 112.6, 84.5, 24.1.

References

[1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 3, p. 428 - 431
[2] European Journal of Organic Chemistry, 2008, # 28, p. 4763 - 4768
[3] Tetrahedron Letters, 1982, vol. 23, # 47, p. 4927 - 4928
[4] Synthetic Communications, 2000, vol. 30, # 5, p. 869 - 875
[5] Arkivoc, 2011, vol. 2011, # 9, p. 51 - 67

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