Synthesis of 2,4,6-trinitrostilbene

Preparation of 2,4,6-trinitrostilbene

Alternative Names: 1,3,5-trinitro-2-(2-phenylethenyl)benzene; Benzene, 1,3,5-trinitro-2-[(1E)-2-phenylethenyl]-; Stilbene, 2,4,6-trinitro-;

Preparation of 2,4,6-trinitrostilbene

Preparation of 2,4,6-trinitrostilbene

To 10 g of 2,4,6-trinitrotoluene dissolved in 25 ml of benzene in a 100 ml round-bottom flask equipped with a reflux condenser, 6 ml of benzaldehyde and 0.5 ml of piperidine are added, and the mixture is refluxed on the water bath for half an hour. The material, while still hot, is poured into a beaker and allowed to cool and crystallize. The crystals, collected on a filter, are rinsed twice with alcohol and recrystallized from a mixture of 2 volumes of alcohol and 1 of benzene. Brilliant yellow glistening needles, m.p. 158° C.

Chemistry of Powder and Explosives, by T. L. Davis, 151, 1941

IUPAC Name

1,3,5-trinitro-2-[(E)-2-phenylethenyl]benzene

InChI

InChI=1S/C14H9N3O6/c18-15(19)11-8-13(16(20)21)12(14(9-11)17(22)23)7-6-10-4-2-1-3-5-10/h1-9H/b7-6+

InChI Key

JHMMNVQXKFUCCZ-VOTSOKGWSA-N

Canonical SMILES

C1=CC=C(C=C1)C=CC2=C(C=C(C=C2[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-]

Isomeric SMILES

C1=CC=C(C=C1)/C=C/C2=C(C=C(C=C2[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-]

Depositor-Supplied Synonyms

1,3,5-trinitro-2-(2-phenylethenyl)benzene, 6307-92-2, NSC43315, AC1NYOAS, Benzene, 1,3,5-trinitro-2-[(1E)-2-phenylethenyl]-, Stilbene, 2,4,6-trinitro-, 1,3,5-trinitro-2- benzene, AC1Q20K1, SCHEMBL7918792, KST-1B7762, AR-1B6332, NSC-43315, 1,3,5-trinitro-2-[(E)-styryl]benzene, OR310894, 1,3,5-trinitro-2-[(E)-2-phenylethenyl]benzene

Removed Synonyms

CID5861124, 6970-78-1

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