 | |||
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| Names | |||
|---|---|---|---|
| IUPAC name Malononitrile[2] | |||
| Preferred IUPAC name Propanedinitrile[2] | |||
| Other names Malonodinitrile, Cyanoacetonitrile, Dicyanomethane, Malonic dinitrile[1] | |||
| Identifiers | |||
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3D model (JSmol) | |||
| 773697 | |||
| ChEBI | |||
| ChemSpider |
| ||
| ECHA InfoCard | 100.003.368 | ||
| EC Number |
| ||
| 1303 | |||
| MeSH | dicyanmethane | ||
| RTECS number |
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| UNII | |||
| UN number | 2647 | ||
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| Properties | |||
| CH2(CN)2 | |||
| Molar mass | 66.063 g·mol−1 | ||
| Appearance | Colourless or white solid[1] | ||
| Density | 1.049 g cm−3 | ||
| Melting point | 32 °C; 89 °F; 305 K | ||
| Boiling point | 220.1 °C; 428.1 °F; 493.2 K | ||
| 13% (20 °C)[1][clarification needed] | |||
| Thermochemistry | |||
| 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 to 188.1 kJ mol−1 | ||
Std enthalpy of combustion(ΔcH⦵298) | −1,654.0 to −1,654.4 kJ mol−1 | ||
| Hazards | |||
| GHS labelling: | |||
  | |||
| Danger | |||
| H301,H311,H331,H410 | |||
| P261,P273,P280,P301+P310,P311 | |||
| Flash point | 86 °C (187 °F; 359 K) | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) |
| ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible) | none[1] | ||
REL (Recommended) | TWA 3 ppm (8 mg/m3)[1] | ||
IDLH (Immediate danger) | N.D.[1] | ||
| Related compounds | |||
Related alkanenitriles | |||
Related compounds | Malonic acid | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Malononitrile is anorganic compoundnitrile with the formulaCH2(CN)2. It is a colorless or white solid, although aged samples appear yellow or even brown. It is a widely used building block inorganic synthesis.
It can be prepared bydehydration ofcyanoacetamide.[3] This method is mainly practiced in China where environmental rules are lax.[citation needed] Most commonly malononitrile is produced by the gas-phase reaction ofacetonitrile andcyanogen chloride:[4]
About 20,000,000 kg are produced annually (2007). Important outlets include the synthesis ofthiamine, the drugtriamterene andminoxidil, and the dyes disperse Yellow 90 and disperse Blue 354.[4]
Malononitrile is relatively acidic, with apKa of 11 in water.[5] This allows it to be used in theKnoevenagel condensation, for example in the preparation ofCS gas:
Despite its relative obscurity, Malononitrile is very useful in several reactions, the prime example being a suitable starting reagent for theGewald reaction, where the nitrile condenses with aketone oraldehyde in the presence of elementalsulfur and a base to produce a 2-aminothiophene.[6]
Due to its permanentdipole moment (i.e., 3.735 ± 0.017 D),[7] malononitrile was detected inspectral emissions coming frominterstellar cloudTMC-1 through theQUIJOTE line survey conducted with theYebes 40 m radio telescope.[8][9]
| Authority control databases: National |
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