A new synthesis of 3,4,5‐triamino‐4H‐1,2,4‐triazole (guanazine)

Synthesis and Characterization of 3,4,5‐Triamino‐1,2,4‐Triazolium 5‐Nitrotetrazolate

“…As described in the literature [3] a mixture of 36.1 g (0.5 mol) dimethylcyanamide 97% (Acros Organics) and 25.5 g (0.5 mol) of hydrazine hydrate 98% (Aldrich) was refluxed for 20 hours. After cooling, the white solid mass recovered was washed with a minimum of 2/1 mixture of (MeOH þ diethyl ether) and filtered off under a nitrogen stream.…”

“…In order to synthesize the target compound 2, 1 was synthesized from dimethylcyanamide and hydrazine as described elsewhere [3]. Compound 1 was then subsequently reacted with ammonium 5-nitrotetrazolate [8 -12] under the loss of ammonia to yield the desired triazolium tetrazolate salt, 2, in good yield according to Scheme 1.…”

“…Much recent interest has been demonstrated in the development of new nitrogen-rich heterocycle-based energetic salts [1,2]. The classic salts (NO 3 À , ClO 4 À , N(NO 2 ) 2 À ) of 1, a triazole containing~74% nitrogen easily synthesized from inexpensive and widely available starting materials [3,4], have been recently reported [5,6] and have generated some interest as new energetic materials. However, the complete characterization of neutral 1 has yet to be reported.…”

Structural and Theoretical Investigation of 3,4,5-Triamino-1,2,4-Triazolium Salts

“…21 Care should be exercised in handling the heterocycle and it should be manipulated under an inert atmosphere at all times as it is sensitive to air oxidation resulting in red colored purchased from Aldrich Chemical Company, and all solvents were degassed using a liquid nitrogen freeze-thaw vacuum procedure. Water was distilled and deionized using a Milli-q-reagent water system (Millipore Corporation, Inc.), and then degassed via multiple freeze-thaw processes under high vacuum.…”

Cyclizations of 3,4,5‐triamino‐s‐triazole (guanazine) and 3,4‐diamino‐5‐mercapto‐s‐triazole with acetic anhydride

“…More recently Gehlen and Robisch (3) have unequivocally synthesized a series of alkyl, aryl and acyl 3 , 5 and 6 substituted s-triazolo [4, 3-b]-s-triazoles by acylation and ring closure of 4,5-diaminos-triazoles. We have now prepared an amino substituted striazolo[4,3b]-s-triazole starting with the readily available guanazine (I) (4).…”