Physical properties
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| Malononitrile forms colorless crystals that are soluble in water, lower alcohols, diethyl ether, and acetonitrile, but insoluble in tetrachloromethane, petroleum ether, and xylene. After prolonged storage the crystals turn yellow to dark brown without significant degradation of quality. |
Chemical properties
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| The chemical properties of malononitrile are determined by the nucleophilicity of the malononitrile anion, formed by deprotonation with relatively weak bases and by the two electrophilic cyano groups. Base-catalyzed dimerization of malononitrile affords 2-amino-1,1,3-tricyano-2-propene. Reaction of malononitrile with trialkyl orthoformates gives (alkoxymethylene)-malononitriles (R1 = OR, R2 = H) which react with nucleophiles by displacement of the alcohol group. Dialkylation of malononitrile with alkyl halides or acylation with acid chlorides and anhydrides is possible. |
Safety and handling
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| Care should be exercised when remelting the solidified product, because spontaneous decomposition can occur when it is exposed for an extended time at elevated temperatures, particularly above 100°C. A water bath is recommended for this purpose. |
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