Malononitrile
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| Malononitrile | |
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| IUPAC name Propanedinitrile[1] | |
| Other names Malonic acid dinitrile[citation needed] | |
| Identifiers | |
| CAS number | 109-77-3  |
| PubChem | 8010 |
| ChemSpider | 13884495  |
| EC number | 203-703-2 |
| UN number | 2647 |
| MeSH | dicyanmethane |
| ChEBI | CHEBI:33186 |
| RTECS number | OO3150000 |
| Beilstein Reference | 773697 |
| Gmelin Reference | 1303 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C3H2N2 |
| Molar mass | 66.06 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 | |
| Std enthalpy of formation ΔfH |
187.7–188.1 kJ mol−1 |
| Std enthalpy of combustion ΔcH |
−1.6540–−1.6544 MJ mol−1 |
| Standard molar entropy S |
130.96 J K−1 mol−1 |
| Specific heat capacity, C | 110.29 J K−1 mol−1 |
| Hazards | |
| GHS pictograms |   |
| GHS signal word | DANGER |
| GHS hazard statements | H301, H311, H331, H410 |
| GHS precautionary statements | P261, P273, P280, P301+310, P311 |
| EU Index | 608-009-00-7 |
| EU classification |  T  N |
| R-phrases | R23/24/25, R50/53 |
| S-phrases | (S1/2), S27, S45 |
| Flash point | 86 °C; 187 °F; 359 K |
| LD50 |
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| Related compounds | |
| Related alkanenitriles | |
| Related compounds | DBNPA |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| Infobox references | |
Malononitrile, also propanedinitrile, is a nitrile 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.; 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.
External links
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