Cyano substituted hydrazines

[hilbert2]

TL;DR

Cyanamide-type compunds from hydrazine, and their potential fuel application

Several articles describe n,n'-dicyanohydrazine being used as a reagent in chemical synthesis. Is there any reason why it would or wouldn't be possible to replace all the H atoms in hydrazine with -CN substituents? That n,n,n',n'-tetracyanohydrazine would look like a potential high energy fuel similar to dicyanoacetylene, which is the substance with highest known flame temperature.

 

[.Scott]

Hydrazine-1_1_2_2 tetracarbonitrile
wikidata
Google says: Based on chemical structure, this compound is likely to be a highly reactive, specialized chemical rather than a commodity chemical, and should be handled with extreme caution in a research environment.

I was unable to find an MSDS (or a vendor) for this chemical.

 

[hilbert2]

Thanks. Just had to find a correct IUPAC name for that chemical to find it, I guess. The PubChem page lists three chemical vendors, and it's said to be a solid with melting point between 70 and 80 degrees Celsius.

Even without any oxidizers mixed with it, that substance is likely to decompose explosively if heated enough, just like hydrazine and acetylene break down to H₂, N₂ and carbon when exposed to electric spark or heating. And small molecule hydrazines are often carcinogenic.

 

[Mayhem]

Please provide a reference to those articles.

 

[hilbert2]

Please provide a reference to those articles.

It's mentioned, for example, in this one: https://connectsci.au/ch/article-ab...nation-Polymer-formed?redirectedFrom=fulltext

In that paper, they describe trying to produce a tetrazole compound, which has a heterocyclic ring with only one carbon atom and four nitrogens, but then get an unexpected reaction product instead.

 

[Mayhem]

It's mentioned, for example, in this one: https://connectsci.au/ch/article-ab...nation-Polymer-formed?redirectedFrom=fulltext

In that paper, they describe trying to produce a tetrazole compound, which has a heterocyclic ring with only one carbon atom and four nitrogens, but then get an unexpected reaction product instead.

This is the only published article I could find, and googling 1,2-dicyanohydrazine (or N,N') only returns a few relevant links, one of which being this exact thread. Certainly an obscure reagent.

Anyway the hydrazine N-N is already reactive and a CN^{1-} group is electron withdrawing. Additional substituon would destabilize the bond furher through delocalization.

 

[hilbert2]

This is the only published article I could find, and googling 1,2-dicyanohydrazine (or N,N') only returns a few relevant links, one of which being this exact thread. Certainly an obscure reagent.

Anyway the hydrazine N-N is already reactive and a CN^{1-} group is electron withdrawing. Additional substituon would destabilize the bond furher through delocalization.

It's in this PubChem entry: https://pubchem.ncbi.nlm.nih.gov/compound/11170913

The patents linked there are written in Chinese or Korean so difficult to read, at least for me. The articles mentioning that compound really seem to just refer to the one I mentioned in the earlier post. But it should be an existing chemical as there seems to be a chemical vendor selling it and the web page mentions physical properties such as melting point and flash point.

If those hydrazine carbonitriles act as good chelating agents, one could probably produce a quite high-energy explosive by complexating something like the Cu²⁺ ion in Cu(ClO₄)₂ with that compound, but can't know how easily it would detonate by accident even from slight friction or heating. Here's an ammonia-complexated version of that: https://onlinelibrary.wiley.com/doi/abs/10.1002/prep.202000131