Malononitrile

Summary

Malononitrile is an organic compound nitrile with the formula CH2(CN)2. It is a colorless or white solid. It can be prepared by dehydration of cyanoacetamide.[3]

Malononitrile
Skeletal formula of malononitrile
Ball and stick model of malononitrile
Spacefill model of malononitrile
Names
IUPAC name
Malononitrile[2]
Preferred IUPAC name
Propanedinitrile[2]
Other names
Malonodinitrile, Cyanoacetonitrile, Dicyanomethane, Malonic dinitrile[1]
Identifiers
  • 109-77-3 checkY
3D model (JSmol)
  • Interactive image
773697
ChEBI
  • CHEBI:33186 ☒N
ChemSpider
  • 13884495 ☒N
ECHA InfoCard 100.003.368 Edit this at Wikidata
EC Number
  • 203-703-2
1303
MeSH dicyanmethane
  • 8010
RTECS number
  • OO3150000
UNII
  • EBL1KKS93J checkY
UN number 2647
  • DTXSID6021907 Edit this at Wikidata
  • InChI=1S/C3H2N2/c4-2-1-3-5/h1H2 ☒N
    Key: CUONGYYJJVDODC-UHFFFAOYSA-N ☒N
  • N#CCC#N
Properties
C3H2N2
Molar mass 66.063 g·mol−1
Appearance Colourless or white solid[1]
Density 1.049 g cm−3
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 to 188.1 kJ mol−1
−1,654.0 to −1,654.4 kJ mol−1
Hazards
GHS labelling:
GHS06: Toxic GHS09: Environmental hazard
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):
  • 19 mg kg−1 (oral, mouse)
  • 350 mg kg−1 (dermal, rat)
NIOSH (US health exposure limits):
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).
☒N verify (what is checkY☒N ?)
Infobox references

Malononitrile is relatively acidic, with a pKa of 11 in water.[4] This allows it to be used in the Knoevenagel condensation, for example in the preparation of CS gas:

CS-chemical-synthesis

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.[5]

See alsoEdit

ReferencesEdit

  1. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0378". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 902. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  3. ^ Surrey, Alexander (1945). "Malononitrile". Organic Syntheses. 25: 63–64. doi:10.15227/orgsyn.025.0063.
  4. ^ Evans pKa table
  5. ^ 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 linksEdit

  • WebBook page for C3H2N2
  • CDC - NIOSH Pocket Guide to Chemical Hazards