Tetrazole 2-methyl-5-nitro

Hie majority of tetrazoles are crystn solids. There is considerable variation in thermal stability, viz. derivatives which melt above 150° do so with decompn, while 5-guanylaminotetrazole (Vol 7, G366-L) does not melt at -300°. In general, most of the tetrazoles are acids and often yield expl salts. The tetrazoles, in the main, can be looked upon as gas generators, useful where instantaneous or progressive pressure effects are required. They possess moderate brisance. However, their salts, which may detonate with extreme brisance, can be used as primary expls, as can 1- and 2-Methyl-5-Nitro Tetrazoles, which are delineated in this article History of Use ... 

Azido-2,2-dimethyl-8-oxo-E16b, 723 (CH - C-N3) lH-Pyrazol 4-Nitro-3(5)-piperidino-E8b, 598 (N02 - NR2) Pyrimidin 5-Ethoxycarbonyl-2-hydrazino-4-methyl- El 6a, 771 (SR - NH-NH2) lH-Tetrazol l-(l-Carboxy-2-methyl-... 

Analog erhalt man 4-Nitro-benzoesaure- (74%), Heptansaure-methylester (86%) und 1-(Benzyloxycarbonyl-methyl)-l,2,3-tetrazol (70%). 

In 2008 Brimble and coworkers examined the effect of a-substitution in proline-based catalysts for the asymmetric aldol addition of acetone to aromatic aldehydes. In the benchmark aldol reaction between acetone and p-nitro-benzaldehyde they observed a remarkable improvement of stereoselectivity using (5 )-a-methyl-tetrazole 9, albeit with longer reaction times caused by the a-geminal disubstitution. Surprisingly 7a afforded a completely racemic product (Scheme 11.7). Using 9 the scope of this reaction was extended efficiently to several other aromatic aldehydes with excellent enantioselectivities (enantiomeric excess — 70-91%). 

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]. 

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