Synthesis of 13C and 15N labeled 2,4-dinitroanisole

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Abstract

Syntheses of [13C6]-2,4-dinitroanisole (ring- 13C6) from [13C6]-anisole (ring-13C6) and [15N2]-2,4- dinitroanisole from anisole using in situ generated acetyl nitrate and [ 15N]-acetyl nitrate, respectively, are described. Treatment of [ 13C6]-anisole (ring-13C6) with acetyl nitrate generated in 100% HNO3 gave [13C 6]-2,4-dinitroanisole (ring-13C6) in 83% yield. Treatment of anisole with [15N]-acetyl nitrate generated in 10 N [15N]-HNO3 gave [15N2]-2,4- dinitroanisole in 44% yield after two cycles of nitration. Byproducts in the latter reaction included [15N]-2-nitroanisole and [ 15N]-4-nitroanisole.

Original languageEnglish (US)
Pages (from-to)434-436
Number of pages3
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume57
Issue number6
DOIs
StatePublished - May 30 2014

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Keywords

  • insensitive munitions compounds
  • synthesis

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Radiology Nuclear Medicine and imaging
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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