Safer and Convenient Synthesis of 3,4-Dicyanofuroxan
Posted on 2019-06-12 - 14:46
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.
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Johnson, Eric C.; Bukowski, Eric J.; Sausa, Rosario C.; Sabatini, Jesse J. (2019). Safer and Convenient Synthesis of 3,4-Dicyanofuroxan. ACS Publications. Collection. https://doi.org/10.1021/acs.oprd.9b00186
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AUTHORS (4)
EJ
Eric C. Johnson
EB
Eric J. Bukowski
RS
Rosario C. Sausa
JS
Jesse J. Sabatini