Malononitrile

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Malononitrile
Skeletal formula of malononitrile
Ball and stick model of malononitrile Spacefill model of malononitrile
Identifiers
CAS number 109-77-3 YesY
PubChem 8010
ChemSpider 13884495 N
EC number 203-703-2
UN number 2647
MeSH dicyanmethane
ChEBI CHEBI:33186 N
RTECS number OO3150000
Beilstein Reference 773697
Gmelin Reference 1303
Jmol-3D images Image 1
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
Specific
heat capacity
C
110.29 J K−1 mol−1
Std molar
entropy
So298
130.96 J K−1 mol−1
Std enthalpy of
formation
ΔfHo298
187.7–188.1 kJ mol−1
Std enthalpy of
combustion
ΔcHo298
−1.6540–−1.6544 MJ mol−1
Hazards
GHS pictograms The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
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 Toxic T Dangerous for the Environment (Nature) N
R-phrases R23/24/25, R50/53
S-phrases (S1/2), S27, S45
Flash point 86 °C (187 °F; 359 K)
LD50
  • 19 mg kg−1 (oral, mouse)
  • 350 mg kg−1 (dermal, rat)
Related compounds
Related alkanenitriles
Related compounds DBNPA
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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:

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.[3]

See also[edit]

References[edit]

  1. ^ "dicyanmethane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 7 June 2012. 
  2. ^ Evans pKa table
  3. ^ 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[edit]