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Synthesis

Safer route to 3,4-dicyanofuroxan

New synthesis of an intermediate used to make explosives sidesteps a violent reaction

by Bethany Halford
June 22, 2019 | APPEARED IN VOLUME 97, ISSUE 25

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The chemists who make explosives and propellants at the US Army Research Laboratory in Maryland are no strangers to dangerous reactions. For example, to prepare 3,4-dicyanofuroxan (DCFO), a common intermediate en route to energetic materials, they’ve had to make the compound in amounts of 5 g or less. That’s because the protocol they use­—which dates back to 1962—can heat up violently and produce noxious gases. Jesse J. Sabatini, a chemist at the lab, says that sometimes while making DCFO, he and his colleagues have had to “close the sash of the hood and walk away until the rather spirited reaction stopped.” There are other methods for preparing DCFO, but these tend to have poor yields, require expensive starting materials, or are difficult to reproduce, Sabatini says. Now, he and his colleagues report a new protocol for making DCFO that can safely be used to make about 60 g of material at a time (Org. Process Res. Dev.2019, DOI: 10.1021/acs.oprd.9b00186). The chemists suspend cyanoacetic acid in dichloromethane and, over 3 h, add a mixture of concentrated sulfuric and nitric acid to the suspension (shown). Their reaction has a 72% yield of DCFO that is 84% pure.

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