5-Aminotetrazole
chemical compound
5-Aminotetrazole is an organic compound with the formula HN4CNH2. It is a white solid that can be obtained both in anhydrous and hydrated forms.
The molecule is planar. The hydrogen bonding pattern in the hydrate supports the assignment of NH being adjacent to carbon in the ring.
Preparation
A synthesis of 5-aminotetrazole through the action of nitrous acid on aminoguanidine was reported by Johannes Thiele in 1892.
The exact structure of the compound was not known at the time, although it was known to crystallize as a monohydrate. The correct structural formula was published in 1901 by Arthur Hantzsch, who obtained it from the reaction between cyanamide and hydrazoic acid.
To avoid direct handling of the problematic hydrazoic acid, a mixture of sodium azide and hydrochloric acid has been used to give the monohydrate at 73% yield.
In a more efficient and controllable one-pot synthesis, cyanamide is treated with hydrazine hydrochloride to give aminoguanidine hydrochloride, which is then diazotized as in Thiele's original process. Addition of ammonia or sodium hydroxide followed by heat-induced cyclization gives the anhydrous product in 74% yield.
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