Succinonitrile

Succinonitrile
Skeletal formula of succinonitrile
Skeletal formula of succinonitrile
Ball and stick model of succinonitrile
Ball and stick model of succinonitrile
Spacefill model of succinonitrile
Spacefill model of succinonitrile
Names
Preferred IUPAC name
Butanedinitrile
Other names
  • Deprelin
  • Dicyanoethane
  • Ethylene cyanide
Identifiers
3D model (JSmol)
1098380
ChemSpider
ECHA InfoCard 100.003.441 Edit this at Wikidata
EC Number
  • 203-783-9
MeSH succinonitrile
RTECS number
  • WN3850000
UNII
  • InChI=1S/C4H4N2/c5-3-1-2-4-6/h1-2H2 checkY
    Key: IAHFWCOBPZCAEA-UHFFFAOYSA-N checkY
  • N#CCCC#N
Properties
C4H4N2
Molar mass 80.090 g·mol−1
Appearance Colorless, waxy crystals
Odor odorless
Density 985 mg mL−1
Melting point 58 °C (136 °F; 331 K)
Boiling point 266.1 °C; 510.9 °F; 539.2 K
130 g L−1
Vapor pressure 300 Pa (at 100 °C)
Thermochemistry
145.60 J K−1 mol−1
191.59 J K−1 mol−1
139.3–140.4 kJ mol−1
−2.2848–−2.2860 MJ mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H315, H319, H335
P261, P305+P351+P338
Flash point 113 °C (235 °F; 386 K)
Lethal dose or concentration (LD, LC):
450 mg kg−1 (oral, rat)
NIOSH (US health exposure limits):
PEL (Permissible)
 none
REL (Recommended)
 TWA 6 ppm (20 mg/m3)
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).
checkY verify (what is checkYX markN ?)

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).

Applications

Succinonitrile may find applications as the "solvent" (while still in its waxy state) in lithium batteries.

Safety

Like most nitriles, succinonitrile is toxic and can release cyanide ions in the body. NIOSH recommends a TWA exposure limit of 6 ppm (20 mg/m³).

See also

References

  1. ↑ 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.
  2. 1 2 3 4 "#0573". NIOSH Pocket Guide to Chemical Hazards. National Institute for Occupational Safety and Health.
  3. ↑ Rubinstein, E. R.; Tirmizi, S. H.; Glicksman, M. E. (1990-11-01). "Long-term purity assessment in succinonitrile". Journal of Crystal Growth. 106 (1): 89–96. Bibcode:1990JCrGr.106...89R. doi:10.1016/0022-0248(90)90290-2. ISSN 0022-0248.
  4. 1 2 "SUCCINONITRILE | CAMEO Chemicals | NOAA". cameochemicals.noaa.gov. Retrieved 2025-11-21.
  5. ↑ PubChem. "Hazardous Substances Data Bank (HSDB) : 7190". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-12-22.
  6. ↑ "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry (7th ed.). Retrieved 2007-09-10.
  7. ↑ Fan, Li-Zhen (August 2007). "Succinonitrile as a Versatile Additive for Polymer Electolytes".{{cite web}}: CS1 maint: url-status (link)