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DOI: 10.1055/s-2004-832822
Malononitrile
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.
-
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