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
3D model (JSmol)
773697
ChEBI
ChemSpider
ECHA InfoCard 100.003.368
EC Number 203-703-2
1303
MeSH dicyanmethane
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
Flash point 86 °C (187 °F; 359 K)
Lethal dose or concentration (LD, LC):
  • 19 mg kg−1 (oral, mouse)
  • 350 mg kg−1 (dermal, rat)
US health exposure limits (NIOSH):
PEL (Permissible)
none[1]
REL (Recommended)
TWA 3 ppm (8 mg/m3)[1]
IDLH (Immediate danger)
N.D.[1]
Related compounds
Related alkanenitriles
Related compounds
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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Infobox references

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

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]

Applications[edit]

Possible uses of malononitrile include in the synthesis of:

  1. Enloplatin
  2. triamterine
  3. Triap
  4. Milrinone

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]