Malononitrile

Malononitrile
IUPAC name

propanedinitrile
Other names

malonic acid dinitrile
Identifiers
CAS number 109-77-3 Y
Jmol-3D images Image 1
Properties
Molecular formula C3H2N2
Molar mass 66.06 g/mol
Appearance crystal
Density 1.1910 g/mL
Melting point

32 °C
Boiling point

220 °C
Solubility in water 13%
Hazards
Main hazards T / N
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Malononitrile, also propanedinitrile, is a nitrile, with formula CH2(CN)2. Malononitrile is relatively acidic, with an pKa of 11 in water.[1] This allows it to be used in the Knoevenagel condensation, for example in the preparation of CS gas:

In related chemistry, malononitrile is a suitable starting material for the Gewald reaction, where the nitrile condenses with a ketone or aldehyde in the presence of elemental sulfur and a base to produce a 2-aminothiophene.[2]

See also

References

  1. ^ Evans pKa table
  2. ^ Sabnis, R.W.; Rangnekar, D.W.; Sonawane, N.D. (1999). "2-Aminothiophenes By The Gewald Reaction". Journal of Heterocyclic Chemistry 36 (2): 333–345. doi:10.1002/jhet.5570360203. http://cat.inist.fr/?aModele=afficheN&cpsidt=10040669. Retrieved 2007-07-18. 

External links