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Author: Subject: Nitrotetrazolate 2N-oxide
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[*] posted on 22-10-2020 at 12:48
Nitrotetrazolate 2N-oxide

Thought I would share this article

Nitro groups are just the kind of bad company I mean, since they both bring their own oxygens to the party and pull electrons around in delightfully destabilizing ways. So nitrotetrazole is already not something I’d feel good about handling (its metal salts are primary explosives), but today’s paper goes a step further and makes an N-oxide out of a nitrogen on a nitrotetrazole ring. This both adds more oxygen and tends to make the crystal packing tighter, which raises the all-important kapow/gram ratio. (There is, of course, little reason to do this unless you feel that life is empty without sudden loud noises). The paper mentions that “Introducing N-oxides onto the tetrazole ring may . . . push the limits of well-explored tetrazole chemistry into a new, unexplored, dimension.”, but (of more immediate importance) it may also push pieces of your lab equipment into unexplored parts of the far wall.
Turns out that you can make the N-oxides through pretty mild chemistry (oxone at room temp)


12.5g of the sodium salt of 5-nitrotetrazole is dissolved in 50mL water, then reacted with 45g of potassium peroxy-monosulfate ("Oxone") and 20g of potassium acetate, which acts as a buffer. The solution is stirred for 24 hours at 50 degC.
A solution containing 0.09 moles of tertiary amine sulfate, such as Et3NH(+), Na(+), SO4(-2), dissolved in 200mL of water, is added. Then the 5-nitro tetrazole-2N-oxide is extracted using 300mL of ethyl acetate. The yellow product moves into the ethyl acetate layer. The 5-nitro tetrazole-2N-oxide product may be purified by crystallization from EtOAc or toluene, resulting in thin yellow crystals. The yield is 70%.

The calculated density for the hydroxylamine salt of 5-nitro tetrazole-2N-oxide is 1.87 g/cm3. The salt has a formula of CN6O4H4. Several salts of the nitrotetrazole oxide anion decomposed at between 153 and 211 degC

[Edited on 22-10-2020 by symboom]
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DBX Labs
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[*] posted on 7-4-2021 at 14:35

What might be the purpose of the tertiary amine sulfate in the proposed oxidation? Is it really all that necessary considering that oxidation of the Ammonium salt is achieved and followed by the immediate extraction of the free acid in ether?

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[*] posted on 9-4-2021 at 02:44

I've been wondering about this too. Maybe its used as a phase transfer catalyst for getting the product more cleanly extracted?
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