Preparation of deuterium-labeled biotransformation products of 2,4,6-trinitrotoluene

Thomas Junk, Jason A. Carr

    Research output: Contribution to journalArticle

    Abstract

    Methods for the preparation of deuterium-labeled analogs to six prominent biotransformation products of the explosive 2,4,6-trinitrotoluene were developed. These are useful as reference standards for stable isotope dilution techniques and for solid state 2H NMR spectroscopic studies. Although syntheses for most of the target compounds in protiated form had been reported in the past, most of those were found to be poorly suited for the preparation of the deuterated materials. Selective reduction of [2H 5]trinitrotoluene furnished [2H5]-4,6-dinitro- 2-hydroxylaminotoluene, [2H5]-2,6-dinitro-4- hydroxylaminotoluene, [2H5]-2-amino-4,6-dinitrotoluene, and [2H5]-4-amino-2,6-dinitrotoluene. The syntheses of [2H10]-2,2′-azo-4,4′,6,6′- tetranitrotoluene and [2H10]-4,4′-azo-2,2′,6, 6′-tetranitrotoluene were accomplished by selective oxidation of [ 2H5]-2-amino-4,6-dinitrotoluene and [2H 5]-4-amino-2,6-dinitrotoluene, respectively.

    Original languageEnglish
    Pages (from-to)344-346
    Number of pages3
    JournalJournal of Labelled Compounds and Radiopharmaceuticals
    Volume56
    Issue number7
    DOIs
    Publication statusPublished - Jun 15 2013

    Fingerprint

    Trinitrotoluene
    Deuterium
    Biotransformation
    Indicator Dilution Techniques
    Isotopes
    Dilution
    Nuclear magnetic resonance
    Oxidation

    Keywords

    • biotransformation
    • degradation
    • explosives
    • trinitrotoluene

    ASJC Scopus subject areas

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

    Cite this

    Preparation of deuterium-labeled biotransformation products of 2,4,6-trinitrotoluene. / Junk, Thomas; Carr, Jason A.

    In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 56, No. 7, 15.06.2013, p. 344-346.

    Research output: Contribution to journalArticle

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