Malononitrile
Appearance
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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 | |||
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 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 | |||
Heat capacity (C)
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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 (187 °F; 359 K) | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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NIOSH (US health exposure limits): | |||
PEL (Permissible)
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none[1] | ||
REL (Recommended)
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TWA 3 ppm (8 mg/m3)[1] | ||
IDLH (Immediate danger)
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N.D.[1] | ||
Related compounds | |||
Related alkanenitriles
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Related compounds
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DBNPA | ||
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 or malonodinitrile, 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:
![CS-chemical-synthesis](http://upload.wikimedia.org/wikipedia/commons/thumb/0/00/CS-Gas-Synthese.svg/600px-CS-Gas-Synthese.svg.png)
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
- ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0378". National Institute for Occupational Safety and Health (NIOSH).
- ^ "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.; Rangnekar, D.W.; Sonawane, N.D. (1999). "2-Aminothiophenes By The Gewald Reaction". Journal of Heterocyclic Chemistry. 36 (2): 333–345. doi:10.1002/jhet.5570360203. Retrieved 2007-07-18.