Malononitrile
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| Names | |||
|---|---|---|---|
| IUPAC name
Propanedinitrile[1]
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| Other names
Malonic acid dinitrile[citation needed]
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| Identifiers | |||
3D model (JSmol)
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| 773697 | |||
| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.003.368 | ||
| EC Number |
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| 1303 | |||
| MeSH | dicyanmethane | ||
PubChem CID
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| RTECS number |
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| UN number | 2647 | ||
CompTox Dashboard (EPA)
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| Properties | |||
| C3H2N2 | |||
| Molar mass | 66.063 g·mol−1 | ||
| Appearance | Colourless crystals | ||
| Density | 1.049 g mL−1 | ||
| Melting point | 32 °C; 89 °F; 305 K | ||
| Boiling point | 220.1 °C; 428.1 °F; 493.2 K | ||
| Thermochemistry | |||
Heat capacity (C)
|
110.29 J K−1 mol−1 | ||
Std molar
entropy (S⦵298) |
130.96 J K−1 mol−1 | ||
Std enthalpy of
formation (ΔfH⦵298) |
187.7–188.1 kJ mol−1 | ||
Std enthalpy of
combustion (ΔcH⦵298) |
−1.6540–−1.6544 MJ mol−1 | ||
| Hazards | |||
| GHS labelling: | |||
 
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| Danger | |||
| H301, H311, H331, H410 | |||
| P261, P273, P280, P301+P310, P311 | |||
| Flash point | 86 °C | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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| Related compounds | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Malononitrile, also propanedinitrile, is a nitrile and cyanocarbon with the formula CH2(CN)2. Malononitrile is relatively acidic, with an pKa of 11 in water.[2] 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.[3]
See also
References
- ^ "dicyanmethane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 7 June 2012.
- ^ Evans pKa table
- ^ Sabnis, R.W. (1999). "2-Aminothiophenes By The Gewald Reaction". Journal of Heterocyclic Chemistry. 36 (2): 333–345. doi:10.1002/jhet.5570360203. Retrieved 2007-07-18.
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