Malononitrile
From Infogalactic: the planetary knowledge core
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| Names | |||
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| IUPAC name
Propanedinitrile[2]
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| Other names
Cyanoacetonitrile, Dicyanomethane, Malonic dinitrile[1]
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| Identifiers | |||
109-77-3  |
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| 773697 | |||
| ChEBI | CHEBI:33186  |
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| ChemSpider | 13884495 |
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| EC Number | 203-703-2 | ||
| 1303 | |||
| Jmol 3D model | Interactive image | ||
| MeSH | dicyanmethane | ||
| PubChem | 8010 | ||
| RTECS number | OO3150000 | ||
| UN number | 2647 | ||
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| Properties | |||
| C3H2N2 | |||
| Molar mass | 66.06 g·mol−1 | ||
| Appearance | Colourless crystals or white powder[1] | ||
| 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 | ||
| 13% (20 °C)[1] | |||
| Thermochemistry | |||
| 110.29 J K−1 mol−1 | |||
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Std molar
entropy (S |
130.96 J K−1 mol−1 | ||
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Std enthalpy of
formation (ΔfH |
187.7–188.1 kJ mol−1 | ||
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Std enthalpy of
combustion (ΔcH |
−1.6540–−1.6544 MJ mol−1 | ||
| Vapor pressure | {{{value}}} | ||
| Related compounds | |||
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Related alkanenitriles
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Related compounds
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DBNPA | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |||
Malononitrile, also propanedinitrile, is a nitrile with the formula CH2(CN)2. Malononitrile is relatively acidic, with a pKa of 11 in water.[3] This allows it to be used in the Knoevenagel condensation, for example in the preparation of CS gas:
File:CS-chemical-synthesis.png
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.[4]
See also
References
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