Malononitrile
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| Malononitrile | |
|---|---|
 |
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| IUPAC name | propanedinitrile |
| Identifiers | |
| CAS number | [109-77-3] |
| SMILES | N#CCC#N |
| 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 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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]
[edit] See also
[edit] References
- ^ Evans pKa table
- ^ Sabnis, R.W.; Rangnekar, D.W.; Sonawane, N.D. (1999). "2-Aminothiophenes By The Gewald Reaction". Journal of Heterocyclic Chemistry 36 (2): 333–345.
[edit] External links
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