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Topic summary

Succinonitrile

Succinonitrile
Names Preferred IUPAC name
Butanedinitrile
Other names
  • Deprelin
  • Dicyanoethane
  • Ethylene cyanide
Identifiers
3D model (JSmol)
1098380 ChemSpider
ECHA InfoCard100.003.441EC Number
  • 203-783-9
MeSHsuccinonitrile
RTECS number
  • WN3850000
UNII
  • InChI=1S/C4H4N2/c5-3-1-2-4-6/h1-2H2
    Key: IAHFWCOBPZCAEA-UHFFFAOYSA-N
  • N#CCCC#N
Properties C4H4N2Molar mass80.090 g·mol Appearance Colorless, waxy crystals Odorodorless Density985 mg mL Melting point58 °C (136 °F; 331 K) Boiling point266.1 °C; 510.9 °F; 539.2 K 130 g L Vapor pressure300 Pa (at 100 °C) Thermochemistry 145.60 J K mol 191.59 J K mol 139.3–140.4 kJ mol −2.2848–−2.2860 MJ mol Hazards GHS labelling: WarningH302, H315, H319, H335P261, P305+P351+P338Flash point113 °C (235 °F; 386 K) Lethal dose or concentration (LD, LC): 450 mg kg (oral, rat)NIOSH (US health exposure limits):
PEL (Permissible)
none
REL (Recommended)
TWA 6 ppm (20 mg/m)
IDLH (Immediate danger)
N.D. 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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Succinonitrile, also butanedinitrile, is a nitrile, with the formula of C2H4(CN)2. It is an odorless, colorless to light brown crystal or colourless waxy solid which melts at 58 °C.

Succinonitrile is produced by the addition of hydrogen cyanide to acrylonitrile (hydrocyanation):

CH2=CHCN + HCN → NCCH2CH2CN

Hydrogenation of succinonitrile yields putrescine (1,4-diaminobutane).

Wikipedia source