%0 Journal Article %A Johnson, Eric C. %A Bukowski, Eric J. %A Sausa, Rosario C. %A Sabatini, Jesse J. %D 2019 %T Safer and Convenient Synthesis of 3,4-Dicyanofuroxan %U https://acs.figshare.com/articles/journal_contribution/Safer_and_Convenient_Synthesis_of_3_4-Dicyanofuroxan/8263766 %R 10.1021/acs.oprd.9b00186.s001 %2 https://acs.figshare.com/ndownloader/files/15451580 %K well-stirred suspension %K HNO %K purity %K Single crystal X-ray diffraction studies %K dropwise addition %K Dropwise treatment %K dicyanofuroxan %K chromatography analysis %K C 4 N 4 O 2 %K scalable synthesis %K refluxing temperature %K self-heating %K dichloromethane %K cyanoacetic acid %K Convenient Synthesis %K method %X A safer, convenient, cost-effective, and scalable synthesis for 3,4-dicyanofuroxan (C4N4O2) is described. Dropwise treatment of a well-stirred suspension of cyanoacetic acid in dichloromethane with concentrated mixed acid (HNO3/H2SO4) 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. %I ACS Publications