Malononitrile

Malononitrile
IUPAC name propanedinitrile
Other names malonic acid dinitrile
Identifiers
CAS number	109-77-3 Y
Jmol-3D images	Image 1
SMILES N#CCC#N
InChI InChI=1/C3H2N2/c4-2-1-3-5/h1H2
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 pK_a 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

• Malonic acid
• Diethyl malonate

References

1. ^ Evans pK_a 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

• WebBook page for C3H2N2