Malononitrile

Malononitrile
Names
IUPAC name
Propanedinitrile[1]
Other names
Cyanoacetonitrile, Dicyanomethane, Malonic dinitrile[2]
Identifiers
3D model (JSmol)
773697
ChEBI
ChemSpider
ECHA InfoCard 100.003.368
EC Number 203-703-2
1303
MeSH dicyanmethane
RTECS number OO3150000
UN number 2647
Properties
C3H2N2
Molar mass 66.06 g·mol−1
Appearance Colourless crystals or white powder[2]
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
13% (20 °C)[2]
Thermochemistry
110.29 J K−1 mol−1
130.96 J K−1 mol−1
187.7–188.1 kJ mol−1
−1.6540–−1.6544 MJ mol−1
Hazards
GHS pictograms
GHS signal word DANGER
H301, H311, H331, H410
P261, P273, P280, P301+310, P311
Flash point 86 °C (187 °F; 359 K)
Lethal dose or concentration (LD, LC):
  • 19 mg kg−1 (oral, mouse)
  • 350 mg kg−1 (dermal, rat)
US health exposure limits (NIOSH):
PEL (Permissible)
 none[2]
REL (Recommended)
 TWA 3 ppm (8 mg/m3)[2]
IDLH (Immediate danger)
 N.D.[2]
Related compounds
Related alkanenitriles
Related compounds
 DBNPA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is ☑Y☒N ?)
Infobox references

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

Malononitrile is relatively acidic, with a pKa of 11 in water.[3] 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.[4]

See also

References

  1. ↑ "dicyanmethane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 7 June 2012.
  2. 1 2 3 4 5 6 "NIOSH Pocket Guide to Chemical Hazards #0378". National Institute for Occupational Safety and Health (NIOSH).
  3. ↑ Evans pKa table
  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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.