HEAT RESISTANT EXPLOSIVES XV. ALTERNATE SYNTHETIC ROUTES TO 3,3'- DIAMINO-2.2', 4.4', 6.6'-HEXANITROBIPHENYL, DIPAM

Abstract

3,3'-Diamino-2,2',4,4',6,6'-hexanitrobiphenyl (DIPAM) has been prepared from m-bromoanisole by a new three step synthesis involving the following reactions: m-broonisole to trinitro-m-bromoanisole which was in turn converted to dimethoxy hexanitrobiphenyl via the Ullmann reaction. Conversion of the dimethoxy derivative to DIPAM was readily achieved by treating it with ammonia in alcohol. A second route, starting with m-bromoaniline via the sequence methyl m-bromophenwith m-bromoaniline via the sequence methyl m-bromo- phenylurethane to methyl trinitrom-bromophenyl urethane to the bis-methyl urethane of DIPAM to DIPAM was also attempted because of its simplicity. However, the sole product isolated from thissequence was picramide.

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Document Details

Document Type
Technical Report
Publication Date
Sep 24, 1962
Accession Number
AD0334076

Entities

People

  • Joseph C. Dacons
  • Lloyd A. Kaplan
  • Robert E. Oesterling

Organizations

  • Naval Ordnance Laboratory

Tags

Communities of Interest

  • Energy and Power Technologies
  • Weapons Technologies

DTIC Thesaurus Topics

  • Alcohols
  • Ammunition
  • Chemical Synthesis
  • Chemistry
  • Copper
  • Ethers
  • Explosives
  • Heat Energy
  • Materials
  • Materials Laboratories
  • Materials Science
  • Munitions
  • Ordnance Laboratories
  • Organic Chemistry
  • United States
  • Weapons

Fields of Study

  • Chemistry

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