A NEW SYNTHESIS FOR 3-CHLORO-2,2',4,4',6,6'-HEXANITROBIPHENYL, PIPICL

Abstract

3-Chloro-2,2',4,4',6,6'-hexanitrobiphenyl, PIPICL, was prepared by a three-step procedure from picryl chloride and m-chloro- or m-bromoanisole. The first step involved the formation of m-picrylanisole by means of a mixed Ullmann reaction. Using 90% nitric acid and 30% oleum, the picrylanisole was nitrated to 3-methoxy-2,2',4,4',6,6'-hexanitrobiphenyl which was in turn converted to PIPICL by treatment with pyridine and phosphorus oxychloride. When m- bromoanisole was used in the Ullmann reaction, the overall yield for the three steps was about 59%. The use of m-chloroanisole resulted in a lower yield in the first step and an overall yield of about 52%. Several variations in procedure are given for the preparation of m-picrylanisole.

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Document Details

Document Type
Technical Report
Publication Date
Jan 18, 1966
Accession Number
AD0370133

Entities

People

  • Joseph C. Dacons
  • Mortimer J. Kamlet

Organizations

  • Naval Ordnance Laboratory

Tags

Communities of Interest

  • Cyber
  • Energy and Power Technologies
  • Weapons Technologies

DTIC Thesaurus Topics

  • Abstracts
  • Acids
  • Alcohols
  • Chemical Synthesis
  • Chemistry
  • Crystallization
  • Distillation
  • Filtration
  • Heat Energy
  • Hydrogen Compounds
  • Materials
  • Munitions
  • Nitric Acid
  • Ordnance Laboratories
  • Organic Chemistry
  • Phase
  • Vacuum Distillation

Fields of Study

  • Chemistry

Readers

  • Organic Chemistry