Diazo transfer reagent 2-azido-4,6-dimethoxy-1,3,5-triazine (ADT) Displays highly exothermic decomposition comparable to tosyl azide
File(s)
Accepted version
Author(s)
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.
Date Issued
2019-05-03
Date Acceptance
2019-04-05
Citation
The Journal of Organic Chemistry, 2019, 84 (9), pp.5893-5898
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
The Royal Society
The Royal Society
The Royal Society
Grant Number
UF140161
RG150444
RGF\EA\180031
Subjects
0304 Medicinal and Biomolecular Chemistry
0305 Organic Chemistry
0302 Inorganic Chemistry
Organic Chemistry
Publication Status
Published
Date Publish Online
2019-04-05