Synthesis of trinitrosotrimethylenetriamine

Preparation of trinitrosotrimethylenetriamine

Alternative Names: Hexahydro-1,3,5-s-triazine; Hexahydro-1,3,5-trinitroso-1,3,5-triazine; 1,3,5-Trinitroso-1,3,5-triazacyclohexane; Hexahydro-1,3,5-trinitroso-s-triazine; 1,3,5-Triazine, hexahydro-1,3,5-trinitroso-;

Preparation of trinitrosotrimethylenetriamine

Preparation of trinitrosotrimethylenetriamine

To a solution of 7 g of hexamethylenetetramine in 200 ml of ice and water, simultaneously a solution were added containing 15 g of sodium nitrite dissolved in 50 ml of water and 6 N hydrochloric acid at the rate required to maintain the pH 1. The mixture was held at 0° C for 30 min.  The precipitated trinitrosotrimethylenetriamine is collected washed with small amount of cold water yielding 50% of the product with melting point 106-107° C.

J. Am. Chem. Soc., 1951, 73 (6), pp 2777–2779

IUPAC Name

1,3,5-trinitroso-1,3,5-triazinane

InChI

InChI=1S/C3H6N6O3/c10-4-7-1-8(5-11)3-9(2-7)6-12/h1-3H2

InChI Key

HFWOSHMLDRSIDN-UHFFFAOYSA-N

Canonical SMILES

C1N(CN(CN1N=O)N=O)N=O

MeSH Synonyms

hexahydro-1,3,5-trinitroso-1,3,5-triazine, TNX cpd, trinitrosotrimethylenetriamine

Depositor-Supplied Synonyms

Trinitrosotrimethylenetriamine, Hexahydro-1,3,5-s-triazine, Hexahydro-1,3,5-trinitroso-1,3,5-triazine, 1,3,5-Trinitroso-1,3,5-triazacyclohexane, Hexahydro-1,3,5-trinitroso-s-triazine, 1,3,5-Triazine, hexahydro-1,3,5-trinitroso-, Trinitrosotrimethylentriamin, 1,3,5-Trinitrosohexahydro-s-triazine, 1,3,5-Trinitroso-1,3,5-triazinane, CHEBI:24557, s-TRIAZINE, HEXAHYDRO-1,3,5-TRINITROSO-, EINECS 237-766-2, Trinitrosotrimethylentriamin [German], TTT, BRN 0014853, 13980-04-6, AC1L1AZO, Ex160, CHEMBL352556, SCHEMBL3464027, CTK4C1953, HFWOSHMLDRSIDN-UHFFFAOYSA-N, AKOS006275535, 1,3,5-Trinitroso-[1,3,5]Triazinane, 1,3,5-Trinitroso-1,3,5-triazinane #, HE037273, HE309657, LS-155437, 1,3,5-Triazine,hexahydro-1,3,5-trinitroso-, 1944-EP2270015A1, N,N’,N”-Trinitroso-1,3,5-hexahydrotriazine, 1,3,5-Trinitroso-1,3,5-triazine, hexahydro-, 4-26-00-00018 (Beilstein Handbook Reference), 3B1-001207

Removed Synonyms

CID26368, c0642, 23374-70-1

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7 comments

  1. Azide

    Just tried this earlier and it worked great. Question- is this especially toxic or carcinogenic? I need to know for safety reasons.

      1. Azide

        Sorry to bother, but one last thing.
        I couldn’t help but notice this molecule is quite similar to RDX (Exceptions obviously being the NO groups are NO2, and the nitrogens [+ the NO2 groups] are in the 2, 4, & 6 positions for RDX, as opposed to 1, 3 & 5 for this compound). Is there a possibility that the NO groups could be either converted or replaced to/with NO2 groups? Thanks!


        1. Post author
          www.PrepChem.com

          Hi

          Thanks for your interest. Yes -NO groups could be converted to NO2 groups, however, the oxidation synthesis is complicated and performed with exotic chemicals (I believe with very concentrated hydrogen peroxide).

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