Safer and Convenient Synthesis of 3,4-Dicyanofuroxan
Eric C. Johnson
Eric J. Bukowski
Rosario C. Sausa
Jesse J. Sabatini
10.1021/acs.oprd.9b00186.s002
https://acs.figshare.com/articles/journal_contribution/Safer_and_Convenient_Synthesis_of_3_4-Dicyanofuroxan/8263769
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.
2019-06-12 14:46:17
well-stirred suspension
HNO
purity
Single crystal X-ray diffraction studies
dropwise addition
Dropwise treatment
dicyanofuroxan
chromatography analysis
C 4 N 4 O 2
scalable synthesis
refluxing temperature
self-heating
dichloromethane
cyanoacetic acid
Convenient Synthesis
method