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Title: Amination of electrophilic aromatic compounds by vicarious nucleophilic substitution

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).

Inventors:
 [1];  [1];  [1]
  1. (Livermore, CA)
Issue Date:
Research Org.:
Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
OSTI Identifier:
873015
Patent Number(s):
6069277
Assignee:
Regents of University of California (Oakland, CA) LLNL
DOE Contract Number:  
W-7405-ENG-48
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
amination; electrophilic; aromatic; compounds; vicarious; nucleophilic; substitution; relates; process; aminate; hydrogen; quaternary; hydrazinium; salts; trialkylhydrazinium; halide; trimethylhydrazinium; iodide; hydroxylamine; alkoxylamines; 4-amino-1; 4-triazole; produce; aminated; structures; 3-diamino-2; 6-trinitrobenzene; datb; 5-triamino-2; tatb; 5-diamino-2; 6-trinitrotoluene; datnt; described; useful; insensitive; explosives; preparation; benzenehexamine; starting; material; synthesis; novel; materials; optical; imaging; devices; liquid; crystals; ferromagnetic; aromatic compound; liquid crystals; imaging devices; optical imaging; imaging device; starting material; aromatic compounds; liquid crystal; novel materials; nucleophilic substitution; vicarious nucleophilic; electrophilic aromatic; /999/

Citation Formats

Mitchell, Alexander R., Pagoria, Philip F., and Schmidt, Robert D. Amination of electrophilic aromatic compounds by vicarious nucleophilic substitution. United States: N. p., 2000. Web.
Mitchell, Alexander R., Pagoria, Philip F., & Schmidt, Robert D. Amination of electrophilic aromatic compounds by vicarious nucleophilic substitution. United States.
Mitchell, Alexander R., Pagoria, Philip F., and Schmidt, Robert D. Sat . "Amination of electrophilic aromatic compounds by vicarious nucleophilic substitution". United States. https://www.osti.gov/servlets/purl/873015.
@article{osti_873015,
title = {Amination of electrophilic aromatic compounds by vicarious nucleophilic substitution},
author = {Mitchell, Alexander R. and Pagoria, Philip F. and Schmidt, Robert D.},
abstractNote = {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).},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2000},
month = {1}
}

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