%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