Malononitrile

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Malononitrile
Skeletal formula of malononitrile
Ball and stick model of malononitrile
Spacefill model of malononitrile
Names
IUPAC name
Propanedinitrile[2]
Other names
Cyanoacetonitrile, Dicyanomethane, Malonic dinitrile[1]
Identifiers
773697
109-77-3 YesY
ChEBI CHEBI:33186 N
ChemSpider 13884495 N
EC number 203-703-2
1303
Jmol-3D images Image
MeSH dicyanmethane
PubChem 8010
RTECS number OO3150000
UN number 2647
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
130.96 J K−1 mol−1
187.7–188.1 kJ mol−1
−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
H301, H311, H331, H410
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)
  • 19 mg kg−1 (oral, mouse)
  • 350 mg kg−1 (dermal, rat)
US health exposure limits (NIOSH):
none[1]
TWA 3 ppm (8 mg/m3)[1]
N.D.[1]
Related compounds
Related alkanenitriles
Related compounds
DBNPA
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
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:

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[edit]

References[edit]

  1. ^ a b c d e f "NIOSH Pocket Guide to Chemical Hazards #0378". National Institute for Occupational Safety and Health (NIOSH). 
  2. ^ "dicyanmethane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 7 June 2012. 
  3. ^ Evans pKa table
  4. ^ 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]