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

J Labelled Comp Radiopharm. 2014 May 30;57(6):434-6. doi: 10.1002/jlcr.3192. Epub 2014 Mar 5.

Abstract

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

Keywords: [13C6]-2,4-dinitroanisole; [15N2]-2,4-dinitroanisole; [15N]-acetyl nitrate; insensitive munitions compounds; synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anisoles / chemical synthesis*
  • Anisoles / chemistry*
  • Carbon Isotopes / chemistry
  • Chemistry Techniques, Synthetic
  • Nitrates / chemistry
  • Nitrogen Isotopes / chemistry
  • Radiochemistry*

Substances

  • Anisoles
  • Carbon Isotopes
  • Nitrates
  • Nitrogen Isotopes
  • 2,4-dinitroanisole