Succinonitrile

Succinonitrile
Ball and stick model of succinonitrile	Spacefill model of succinonitrile
Names
	Preferred IUPAC name Butanedinitrile
	Other names Deprelin; Dicyanoethane; Ethylene cyanide;
Identifiers
CAS Number	110-61-2 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1098380
ChemSpider	21106481 ;
ECHA InfoCard	100.003.441
EC Number	203-783-9;
MeSH	succinonitrile
PubChem CID	8062;
RTECS number	WN3850000;
UNII	1R479O92DO ;
CompTox Dashboard (EPA)	DTXSID9026059 ;
	InChI InChI=1S/C4H4N2/c5-3-1-2-4-6/h1-2H2 Key: IAHFWCOBPZCAEA-UHFFFAOYSA-N ;
	SMILES N#CCCC#N;
Properties
Chemical formula	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
Solubility in water	130 g L−1
Vapor pressure	300 Pa (at 100 °C)
Thermochemistry
Heat capacity (C)	145.60 J K−1 mol−1
Std molar; entropy (S⦵298)	191.59 J K−1 mol−1
Std enthalpy of; formation (ΔfH⦵298)	139.3–140.4 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−2.2848–−2.2860 MJ mol−1
Hazards
	GHS labelling:
Pictograms
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−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	Propanenitrile; Aminopropionitrile; Pivalonitrile; Acetone cyanohydrin; Butyronitrile; Tetramethylsuccinonitrile;
Related compounds	DBNPA
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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):^[4]

CH₂=CHCN + HCN → NCCH₂CH₂CN

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

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

[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.

[PGCH-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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