Malononitrile

Malononitrile

Names
IUPAC name Propanedinitrile
Other names Cyanoacetonitrile, Dicyanomethane, Malonic dinitrile
Identifiers
CAS Number	109-77-3 Y
3D model (Jmol)	Interactive image
Beilstein Reference	773697
ChEBI	CHEBI:33186 N
ChemSpider	13884495 N
ECHA InfoCard	100.003.368
EC Number	203-703-2
Gmelin Reference	1303
MeSH	dicyanmethane
PubChem CID	8010
RTECS number	OO3150000
UN number	2647
InChI InChI=1S/C3H2N2/c4-2-1-3-5/h1H2 N Key: CUONGYYJJVDODC-UHFFFAOYSA-N N
SMILES N#CCC#N
Properties
Chemical formula	C3H2N2
Molar mass	66.06 g·mol−1
Appearance	Colourless crystals or white powder
Density	1.049 g mL−1
Melting point	32 °C; 89 °F; 305 K
Boiling point	220.1 °C; 428.1 °F; 493.2 K
Solubility in water	13% (20 °C)
Thermochemistry
Specific heat capacity (C)	110.29 J K−1 mol−1
Std molar entropy (So298)	130.96 J K−1 mol−1
Std enthalpy of formation (ΔfHo298)	187.7–188.1 kJ mol−1
Std enthalpy of combustion (ΔcHo298)	−1.6540–−1.6544 MJ mol−1
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H301, H311, H331, H410
GHS precautionary statements	P261, P273, P280, P301+310, P311
EU classification (DSD)	T N
R-phrases	R23/24/25, R50/53
S-phrases	(S1/2), S27, S45
Flash point	86 °C (187 °F; 359 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	19 mg kg−1(oral, mouse) 350 mg kg−1(dermal, rat)
US health exposure limits (NIOSH):
PEL (Permissible)	none
REL (Recommended)	TWA 3 ppm (8 mg/m3)
IDLH (Immediate danger)	N.D.
Related compounds
Related alkanenitriles	Acetonitrile Aminoacetonitrile Glycolonitrile Cyanogen Propanenitrile Aminopropionitrile Pivalonitrile Acetone cyanohydrin Butyronitrile Succinonitrile Tetramethylsuccinonitrile
Related compounds	DBNPA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Malononitrile, also propanedinitrile or malonodinitrile, is a nitrile with the formula CH₂(CN)₂.

Malononitrile is relatively acidic, with a pK_a of 11 in water. This allows it to be used in the Knoevenagel condensation, for example in the preparation of CS gas:

In related chemistry, malononitrile is a suitable starting material for the Gewald reaction, where the nitrile condenses with a ketone or aldehyde in the presence of elemental sulfur and a base to produce a 2-aminothiophene.

Possible uses of malononitrile include in the synthesis of Enloplatin, triamterine & Triap.