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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Nitrates
Nitration
Byproducts
anisole
2,4-dinitroanisole

Keywords

  • insensitive munitions compounds
  • synthesis

ASJC Scopus subject areas

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

Cite this

@article{1aeeeea61adf48fc856f34f0147bc725,
title = "Synthesis of 13C and 15N labeled 2,4-dinitroanisole",
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.",
keywords = "insensitive munitions compounds, synthesis",
author = "Bhumasamudram Jagadish and Field, {James A} and Jon Chorover and {Sierra Alvarez}, {Maria Reye} and Abrell, {Leif M} and Mash, {Eugene A}",
year = "2014",
month = "5",
day = "30",
doi = "10.1002/jlcr.3192",
language = "English (US)",
volume = "57",
pages = "434--436",
journal = "Journal of Labelled Compounds and Radiopharmaceuticals",
issn = "0362-4803",
publisher = "John Wiley and Sons Ltd",
number = "6",

}

TY - JOUR

T1 - Synthesis of 13C and 15N labeled 2,4-dinitroanisole

AU - Jagadish, Bhumasamudram

AU - Field, James A

AU - Chorover, Jon

AU - Sierra Alvarez, Maria Reye

AU - Abrell, Leif M

AU - Mash, Eugene A

PY - 2014/5/30

Y1 - 2014/5/30

N2 - 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.

AB - 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.

KW - insensitive munitions compounds

KW - synthesis

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U2 - 10.1002/jlcr.3192

DO - 10.1002/jlcr.3192

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JO - Journal of Labelled Compounds and Radiopharmaceuticals

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