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Succinonitrile

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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
CAS Number
3D model (JSmol)
Beilstein Reference 1098380
ChemSpider
ECHA InfoCard 100.003.441 Edit this at Wikidata
EC Number
  • 203-783-9
MeSH succinonitrile
PubChem CID
RTECS number
  • WN3850000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H4N2/c5-3-1-2-4-6/h1-2H2Key: IAHFWCOBPZCAEA-UHFFFAOYSA-N
SMILES
  • N#CCCC#N
Properties
Chemical formula C4H4N2
Molar mass 80.090 g·mol
Appearance Colorless, waxy crystals
Odor odorless
Density 985 mg mL
Melting point 58 °C (136 °F; 331 K)
Boiling point 266.1 °C; 510.9 °F; 539.2 K
Solubility in water 130 g L
Vapor pressure 300 Pa (at 100 °C)
Thermochemistry
Heat capacity (C) 145.60 J K mol
Std molar
entropy (S298) 		191.59 J K mol
Std enthalpy of
formation (ΔfH298) 		139.3–140.4 kJ mol
Std enthalpy of
combustion (ΔcH298) 		−2.2848–−2.2860 MJ mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302, H315, H319, H335
Precautionary statements P261, P305+P351+P338
Flash point 113 °C (235 °F; 386 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose) 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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Succinonitrile, also butanedinitrile, is a nitrile, with the formula of C2H4(CN)2. It is a colorless 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).

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. ^ NIOSH Pocket Guide to Chemical Hazards. "#0573". National Institute for Occupational Safety and Health (NIOSH).
  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. "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry (7th ed.). Retrieved 2007-09-10.

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