Succinonitrile

Succinonitrile

Names
IUPAC name Butanedinitrile
Other names Deprelin Dicyanoethane Ethylene cyanide
Identifiers
CAS Number	110-61-2 Y
3D model (Jmol)	Interactive image
Beilstein Reference	1098380
ChemSpider	21106481 Y
ECHA InfoCard	100.003.441
EC Number	203-783-9
MeSH	succinonitrile
PubChem	8062
RTECS number	WN3850000
UNII	1R479O92DO Y
InChI InChI=1S/C4H4N2/c5-3-1-2-4-6/h1-2H2 Y Key: IAHFWCOBPZCAEA-UHFFFAOYSA-N Y
SMILES N#CCCC#N
Properties
Chemical formula	C4H4N2
Molar mass	80.09 g·mol−1
Appearance	Colorless, waxy crystals
Odor	odorless
Density	985 mg mL−1
Melting point	52 to 62 °C; 125 to 143 °F; 325 to 335 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
Specific heat capacity (C)	145.60 J K−1 mol−1
Std molar entropy (So298)	191.59 J K−1 mol−1
Std enthalpy of formation (ΔfHo298)	139.3–140.4 kJ mol−1
Std enthalpy of combustion (ΔcHo298)	−2.2848–−2.2860 MJ mol−1
Hazards
GHS pictograms
GHS signal word	WARNING
GHS hazard statements	H302, H315, H319, H335
GHS precautionary statements	P261, P305+351+338
EU classification (DSD)	Xn
R-phrases	R22, R36/37/38
S-phrases	S26, S36/37, S45
Flash point	113 °C (235 °F; 386 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	450 mg kg−1(oral, rat)
US health exposure limits (NIOSH):
PEL (Permissible)	none
REL (Recommended)	TWA 6 ppm (20 mg/m3)
IDLH (Immediate danger)	N.D.
Related compounds
Related alkanenitriles	Propanenitrile Aminopropionitrile Malononitrile Pivalonitrile Acetone cyanohydrin Butyronitrile Tetramethylsuccinonitrile Glutaronitrile
Related compounds	DBNPA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Succinonitrile, also butanedinitrile, is a nitrile, with the formula of C₂H₄(CN)₂. It is a colorless solid that melts at 57 °C, hence its waxy consistency.

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

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