Safer and Convenient Synthesis of 3,4-Dicyanofuroxan

Published on 2019-06-12T14:46:18Z (GMT) by
A safer, convenient, cost-effective, and scalable synthesis for 3,4-dicyanofuroxan (C<sub>4</sub>N<sub>4</sub>O<sub>2</sub>) is described. Dropwise treatment of a well-stirred suspension of cyanoacetic acid in dichloromethane with concentrated mixed acid (HNO<sub>3</sub>/H<sub>2</sub>SO<sub>4</sub>) affords dicyanofuroxan in 72% yield and in 84% purity after liquid chromatography analysis. Single crystal X-ray diffraction studies further confirm the product and yield its molecular conformation and crystal packing. During the dropwise addition of mixed acid, self-heating occurs, and this event is necessary for the reaction to adequately proceed. However, such self-heating is limited to the refluxing temperature of dichloromethane. This new method supersedes the previous methods used to synthesize dicyanofuroxan, which were low-yielding and of significantly lower purity, irreproducible, relied on expensive reagents, and suffered from dangerous exothermic profiles.

Cite this collection

Johnson, Eric C.; Bukowski, Eric J.; Sausa, Rosario C.; Sabatini, Jesse J. (2019): Safer and Convenient Synthesis of 3,4-Dicyanofuroxan. ACS Publications. Collection.