Malononitrile

Malononitrile
Ball and stick model of malononitrile	Spacefill model of malononitrile
Names
	IUPAC name Propanedinitrile
	Other names Cyanoacetonitrile, Dicyanomethane, Malonic dinitrile
Identifiers
CAS Number	109-77-3 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	773697
ChEBI	CHEBI:33186 ;
ChemSpider	13884495 ;
ECHA InfoCard	100.003.368
EC Number	203-703-2;
Gmelin Reference	1303
MeSH	dicyanmethane
PubChem CID	8010;
RTECS number	OO3150000;
UN number	2647
CompTox Dashboard (EPA)	DTXSID6021907 ;
	InChI InChI=1S/C3H2N2/c4-2-1-3-5/h1H2 Key: CUONGYYJJVDODC-UHFFFAOYSA-N ;
	SMILES N#CCC#N;
Properties
Chemical formula	C3H2N2
Molar mass	66.063 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
Heat capacity (C)	110.29 J K−1 mol−1
Std molar; entropy (S⦵298)	130.96 J K−1 mol−1
Std enthalpy of; formation (ΔfH⦵298)	187.7–188.1 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−1.6540–−1.6544 MJ mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H331, H410
Precautionary statements	P261, P273, P280, P301+P310, P311
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);
	NIOSH (US health exposure limits):
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). verify (what is ?) Infobox references

Malononitrile, also propanedinitrile, is a nitrile with the formula CH₂(CN)₂. Malononitrile is relatively acidic, with a pK_a of 11 in water.^[3] This allows it to be used in the Knoevenagel condensation, for example in the preparation of CS gas:

File:CS-chemical-synthesis.png

CS-chemical-synthesis

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.^[4]

References

^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0378". National Institute for Occupational Safety and Health (NIOSH).
^ "dicyanmethane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 7 June 2012.
^ Evans pK_a table
^ Sabnis, R.W.; Rangnekar, D.W.; Sonawane, N.D. (1999). "2-Aminothiophenes By The Gewald Reaction". Journal of Heterocyclic Chemistry. 36 (2): 333–345. doi:10.1002/jhet.5570360203. Retrieved 2007-07-18.

External links

[PGCH-1] ^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0378". National Institute for Occupational Safety and Health (NIOSH).

[2] "dicyanmethane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 7 June 2012.

[3] Evans pK_a table

[Sabnis1999-4] Sabnis, R.W.; Rangnekar, D.W.; Sonawane, N.D. (1999). "2-Aminothiophenes By The Gewald Reaction". Journal of Heterocyclic Chemistry. 36 (2): 333–345. doi:10.1002/jhet.5570360203. Retrieved 2007-07-18.

[2]

[1]

[3]

[4]

See also

References

External links