Amination of electrophilic aromatic compounds by vicarious nucle

Details Amination of electrophilic aromatic compounds by vicarious nucle Amination of electrophilic aromatic compounds by vicarious nucle

1997-11-12

2000-05-30

Burn, Brian M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

564408, 564441, 568932, 568934, C07C20902

Patent

active

060692774

ABSTRACT:
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).

REFERENCES:
patent: 4032377 (1977-06-01), Benziger et al.

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