Synlett 2004(12): 2247-2248  
DOI: 10.1055/s-2004-832822
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Malononitrile

Anil Saikia*
C/O Dr. Romesh Chandra Boruah, Medicinal Chemistry Division, Regional Research Laboratory, Jorhat, Assam, 785006, India
e-Mail: anil_saikia@yahoo.co.in;
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
21. September 2004 (online)

The weak cyanocarbon malononitrile [CH2(CN)2] is a colourless solid with a melting range of 32-34 °C and a boiling range of 218-219 °C. It is a versatile compound of exceptional reactivity. Malononitrile can be prepared in 80-96% yield by the reaction of cyanoacetamide and POCl3 or PCl5 in presence of inorganic salts. [1-2] Due to the presence of active methylene protons, the reagent is found to be more useful in carbon-carbon bond formation reactions. It is used extensively [3] as a reactant or reaction intermediate, since the methylene group and one or both cyano groups can take part in condensation reactions to give a variety of addition products and heterocyclic compounds. This unique reactivity makes malononitrile an important chemical in research and in medical, industrial and agricultural chemistry applications.

    References

  • 1a Surrey AR. Organic Synthesis Coll. Vol. III   John Wiley and Sons; New York: 1944.  p.535 
  • 1b Corson BB. Scott RW. Vose CE. Organic Synthesis Coll. Vol. II   John Wiley and Sons; New York: 1943.  p.379 
  • 2 Fahrenbach MJ. inventors; US Patent  2,459,128.  1949. Chem. Abstr. 1949, 43, 3470
  • 3 Freeman F. Chem. Rev.  1969,  69:  591 
  • 4 Shestopalov A. Rodinovskaya L. Shestopalov A. Zlotin S. Nesterov V. Synlett  2003,  2309 
  • 5 Jin T.-S. Wang AQ. Wang AX. Zhang JS. Li TS. Synlett  2004,  871 
  • 6 Maggi R. Ballini R. Sartory G. Sartory R. Tetrahedron Lett.  2004,  45:  2297 
  • 7 Saikia A. Chetia A. Bora U. Boruah RC. Synlett  2003,  1506 
  • 8 Mont N. Texido J. Borrel JI. Kappe CO. Tetrahedron Lett.  2003,  44:  5385 
  • 9a Ayoubi S. Abdullah E. Texier-Boullet F. Hamelin J. Synthesis  1994,  258 
  • 9b Prajapati D. Lekhok KC. Sandhu JS. Ghosh AC. J. Chem. Soc., Perkin Trans. 1  1996,  959 
  • 10 Sharma U. Ahmed S. Boruah RC. Tetrahedron Lett.  2000,  41:  3493 
  • 11 Gao C. Tao X. Qian Y. Huang J. Chem. Commun.  2003,  1444