Amination of electrophilic aromatic compounds by vicarious nucleophilic substitution
The present invention relates to a process to aminate electrophilic aromatic compounds by vicarious nucleophilic substitution of hydrogen using quaternary hydrazinium salts. The use of trialkylhydrazinium halide, e.g., trimethylhydrazinium iodide, as well as hydroxylamine, alkoxylamines, and 4-amino-1,2,4-triazole to produce aminated aromatic structures, such as 1,3-diamino-2,4,6-trinitrobenzene (DATB), 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) and 3,5-diamino-2,4,6-trinitrotoluene (DATNT), is described. DATB and TATB are useful insensitive high explosives. TATB is also used for the preparation of benzenehexamine, a starting material for the synthesis of novel materials (optical imaging devices, liquid crystals, ferromagnetic compounds).
- Research Organization:
- Lawrence Livermore National Laboratory (LLNL), Livermore, CA
- Sponsoring Organization:
- US Department of Energy
- DOE Contract Number:
- W-7405-ENG-48
- Assignee:
- LLNL; EDB-00:033428
- Patent Number(s):
- NONE
- Application Number:
- Int. Cl. C07C 209/02; US 6,069,277/A/; 8-967,914
- OSTI ID:
- 20050822
- Country of Publication:
- United States
- Language:
- English
Similar Records
New aminating reagents forthe synthesis of 1,3,5-Triamino-2,4,6-Trinitrobenzene (TATB) and other insensitive energetic materials
Conversion of the rocket propellant UDMH to a reagent useful in vicarious nucleophilic substitution reactions