Malononitrile

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Malononitrile
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Identifiers
CAS number 109-77-3
SMILES N#CCC#N
InChI InChI=1/C3H2N2/c4-2-1-3-5/h1H2
Properties
Molecular formula C3H2N2
Molar mass 66.06 g/mol
Melting point

32 °C

Boiling point

220 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and 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:

CS-chemical-synthesis

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

Reference

  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. Retrieved on 2007-07-18.

External links


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