The anion can be obtained by reacting squaric acid with n-butanol to obtain the diester1,2-dibutyl squarate (an oily orange liquid) and treating the latter with metallic sodium and malononitrile (N≡C−)2CH2 to give the trihydrated disodium salt 2Na+·C 10N 4O2− 2·3H2O, a yellow water-soluble solid. The hydrated salt loses the water below 100 °C, but the resulting anhydrous salt is stable up to 400 °C.[1]
Salts
Reaction of the sodium salt with the chlorides of other cations in ethanol affords the following salts:[1]
^ abcVanessa E. de Oliveira, Gustavo S. de Carvalho, Maria I. Yoshida, Claudio L. Donnici, Nivaldo L. Speziali, Renata Diniz and Luiz Fernando C. de Oliveira (2009), "Bis(dicyanomethylene)squarate squaraines in their 1,2- and 1,3-forms: Synthesis, crystal structure and spectroscopic study of compounds containing alkali metals and tetrabutylammonium ions." Journal of Molecular Structure Volume 936, Issues 1–3, Pages 239–249 doi:10.1016/j.molstruc.2009.08.002
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