Nitro triazolone

The 3-(4-chloro-2-nitrophenyl)triazole derivative (110) undergoes nucleophilic displacement of chloride by azide ion <89JCS(P2)1425>. The thermal and photochemical decomposition of 3-nitro-triazolone have been shown to occur via radical cations <9UPC5509>. 

There is a drive to develop insensitive or less sensitive munitions, ie, those less likely to accidental or sympathetic detonation. A leading candidate is 3-nitro-l,2,4-triazolin-5-one [930-33-6] (59), made by the reaction of semicarbazide and formic acid to give l,2,4-triazolin-5-one [932-64-9] foUowed by nitration of the triazolone (218). 

Dinitroazetidine salts were studied as explosives nitrate, dinitroimidate, 2,4-dinitroimidazolate, 4,4, 5.5 -tctranitro-2.2 -biimidazolate, 5-nitro-l,2,4-triazolonate... 

Methyl 3,3-diazido-2-cyanoacrylate, 1824 Methylenebis(3 -nitramino-4-methylfurazan), 2805 1-Methyl-1,2,3-triazole, 1189 Nitrosyl azide, 4766 3-Nitro-l,2,4-triazolone, 0716 Pentazole, 4443... 

Methoxy-l,2,3,4-thiatriazole, 0773 1-Methyl-l,2,3-triazole, 1189 4-Nitroamino-1,2,4-triazole, 0777 4-Nitro-l-picryl-l,2,3-triazole, 2886 3-Nitro-l,2,4-triazolone, 0716 1-Picryl-l,2,3-triazole, 2893... 

Oxynitrotriazole, see 3-Nitro-l,2,4-triazolone, 0712 Ozobenzene, see Benzene triozonide, 2336... 

Nitro-l,2,4-triazolone, 0712 Nitroacetaldehyde, 0759 2-Nitroethanol, 0867 2-Nitroethanonitrile, 0707 Nitromethane, 0455 5-Nitrotetrazole, 0386 Potassium 1-nitroethoxide, 0802 Potassium 2,5-dinitrocyclopentanonide, 1841 Sodium 5-nitrotetrazolide, 0544... 

It is not possible to introduce a nitro group into the 1,2,4-triazole ring by the action of the sulfuric-nitric acid mixture because of the disactivation of the cycle by two pyridine nitrogen atoms furthermore, their disactivation effect is aggravated by the heterocycle protonation in the acid medium. The only exception is the nitration of l,2,4-triazolon-5 [250-264], This is probably due to the specific electronic structure of the substrate (the azolone form) (Scheme 32). 

Nitro-l,2,4-triazolon-5 (NTO) is one of the popular and widely used in the last time the explore compound [263-268],... 

During the nitration of azoles with an unsubstituted pyrrole heteroatom under these conditions it is often possible to isolate the A-nitroazoles. Thus, with acetylnitrate in glacial acetic acid it was possible to obtain A-nitropyrazoles [63,307-317], A-nitro-1,2,4-triazoles [318, 319], and A-nitro-1,2,4-triazolon-5 [264] (Scheme 33). 

C NMR spectra of 3-nitro-l,2,4-triazol-5-one and seven of its salts with different amines have been studied. The chemical shifts of C-3 and C-5 are independent of the nature of the cation (Table 3.21) [560], NMR spectra of 1-nitro-1,4-dihydro-1-7/-l,2,4-triazol-5-one, 5-(3-azido-l,2,4-triazol-3-yl)-3-nitro-l,2,4-triazoles [611], l-alkyl-3-nitro-l,2,4-triazol-5-one [612], some 3-nitro-2-methyl-l,2,4-triazolone derivatives [613-615], and their mono- and dinitro energetic salts [616] have been discussed. 

Influence of pH medium on the UV-absorption spectra of 5-nitro-l,2,4-triazole, 3-methyl-5-nitro-l,2,4-triazole, 4-nitro-2-(l,2,4-triazole-3-yl)-l,2,3-triazole and nitroderivatives of l,2,4-triazolone-5 [611, 613,1180] has been considered. 

It is known that 3-nitro-l,2,4-triazolon-5 is one of the most popular and widely used explosive compounds. Currently, wide possibilities of the preparation of new high-density energetic compounds on the base nitrofurazans and nitrofuroxans obtained by oxidation of the corresponding aminooxadiazoles in the presence of mainly H202/H2S04 are opened up. 

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