Organic Derivatives of 5-Nitrotetrazole

The organic derivatives of 5-nitrotetrazole form two isomers substituted either in position 1 or 2 of the ring. Some attention has been given to methyl-5-nitrotetrazoles and to 2-picryl-5-nitrotetrazole. The melting point of l-methyl-5-nitrotetrazole is 56 °C and of 2-methyl-5-nitrotetrazole is 86 °C. However 2-methyl-5-nitrotetrazole was found not to initiate RDX in a commercial detonator setup. 5-Nitro-2-(2,4,6-trinitrofenyl)tetrazole (subsequently just 5-nitro-2-picryltetrazole) has the characteristics of primary explosives but unfortunately is very sensitive to friction. The p-nitrobenzyl derivate of 5-nitrotetrazole is not a primary explosive and behaves more like a secondary explosive [4]. 

Alkyl derivatives of 5-nitrotetrazole form by alkylation of the metallic salts of 5-nitrotetrazole (e.g., sodium, silver) by alkyUialogenide [4]. 

The alkylation leads to a mixture of isomers with the methyl group in positions 

1 and 2. Electronegative substituent on carbon makes substitution in position 

2 predominant. The methyl derivate is formed according to the reaction shown, but the ethyl, propyl, and isopropyl derivatives could not be isolated (silver salt of 5-nitro-l//-nitrotetrazole was used for synthesis) by Bates and Jenkins [4]. 

---