Russian Journal of Applied Chemistry, 2009, Vol. 82, No. 10, pp. 1802−1804.
Pleiades Publishing, Ltd., 2009.
Original Russian Text A.V. Shastin, B.L. Korsunskii, T.I. Godovikova, V.P. Lodygina, 2009, published in Zhurnal Prikladnoi Khimii, 2009, Vol. 82, No. 10,
STUDIES IN THE FIELD OF CHEMISTRY OF NITRO COMPOUNDS
(TO 100TH BIRTHDAY ANNIVERSARY OF S. S. NOVIKOV)
Synthesis of 5-Dinitromethyltetrazole
A. V. Shastin, B. L. Korsunskii, T. I. Godovikova, and V. P. Lodygina
Institute of Chemical Physics Problems, Russian Academy of Sciences, Chernogolovka, Russia
Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Received April 29, 2009
Abstract—A convenient method of synthesizing 5-dinitromethyltetrazole on the basis of 1,1-diamino-2,2-
dinitroehtilene was developed.
Several methods of synthesizing 5-dinitromethyl-
tetrazole (I) have been published . The ﬁ rst method
is the synthesis from dinitroacetonitrile ammonium salts
(II), which, however, results in a low yield (8.8%) of
the target tetrazole and is complicated by a necessity of
removing bitetrazole (III) formed simultaneously 
In  the reducing denitration of explosive 5-tri-
nitromethyltetrazole (IV) is used (Scheme 2).
The method of obtaining monosodium tetrazole salt
(VI) from amidrazone of dinitroacetic acid (V) was
described  (Scheme 3).
However it is hardly possible to consider this method
as comprehensible because of unpredictable behavior of
amidrazone (V): an occasion of spontaneous explosive
decomposition of this compound was described .
Recently the two-stage method  of obtaining tetrazole
(I) from ethyl ether of tetrazole-5-ylacetic acid (VII) was
proposed, and it is highly probable that the intermediately
separated product, ethyl ether of dinitrotetrazolylacetic
acid (VIII), is fairly sensitive (Scheme 4).
A convenient method of the synthesis of 5-di-
nitromethyltetrazole (DMT) from 1,1-diamino-2,2-
dinitroethylene (IX) through salt (X) without the
intermediate isolation of explosive amidrazone (V) was
developed, which allows obtaining target tetrazole with
a high yield (Scheme 5). To carry out the reaction, it is
necessary to use three equivalents of sodium nitrite, and
in this case formed azide ions are decomposed up to