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Diazo transfer reagent 2-azido-4,6-dimethoxy-1,3,5-triazine (ADT) Displays highly exothermic decomposition comparable to tosyl azide

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Title: Diazo transfer reagent 2-azido-4,6-dimethoxy-1,3,5-triazine (ADT) Displays highly exothermic decomposition comparable to tosyl azide
Authors: Green, SP
Payne, AD
Wheelhouse, KM
Hallett, JP
Miller, PW
Bull, JA
Item Type: Journal Article
Abstract: 2-Azido-4,6-dimethoxy-1,3,5-triazine (ADT) was reported recently as a new “intrinsically safe” diazo-transfer reagent. This assessment was based on differential scanning calorimetry data indicating that ADT exhibits endothermic decomposition. We present DSC data on ADT that show exothermic decomposition with an initiation temperature (Tinit) of 159 °C and an enthalpy of decomposition (ΔHD) of −1135 J g–1 (−207 kJ mol–1). We conclude that ADT is potentially explosive and must be treated with caution, being of comparable exothermic magnitude to tosyl azide (TsN3). A maximum recommended process temperature for ADT is 55 °C.
Issue Date: 3-May-2019
Date of Acceptance: 5-Apr-2019
URI: http://hdl.handle.net/10044/1/69739
DOI: https://dx.doi.org/10.1021/acs.joc.9b00269
ISSN: 0022-3263
Publisher: American Chemical Society (ACS)
Start Page: 5893
End Page: 5898
Journal / Book Title: The Journal of Organic Chemistry
Volume: 84
Issue: 9
Copyright Statement: © 2019 American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, after peer review and technical editing by the publisher. To access the final edited and published work see https://dx.doi.org/10.1021/acs.joc.9b00269
Sponsor/Funder: The Royal Society
The Royal Society
The Royal Society
Funder's Grant Number: UF140161
RG150444
RGF\EA\180031
Keywords: 0304 Medicinal and Biomolecular Chemistry
0305 Organic Chemistry
0302 Inorganic Chemistry
Organic Chemistry
Publication Status: Published
Embargo Date: 2020-04-05
Online Publication Date: 2019-04-05
Appears in Collections:Chemistry
Catalysis and Advanced Materials
Chemical Engineering
Faculty of Natural Sciences



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