Diazo Transfer Reagent 2-Azido-4,6-Dimethoxy-1,3,5-Triazine (ADT) Displays Highly Exothermic Decomposition Comparable to Tosyl Azide
DOI: 10.14469/hpc/4946 Metadata
Created: 2019-01-15 14:54
Last modified: 2019-04-08 17:48
License: Creative Commons: Public Domain Dedication 1.0
Funding: (none given)
Co-author: James A. Bull Co-author: Jason Hallett Co-author: Philip Miller
Description
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 (DSC) 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 of -1135 J/g (-207 kJ/mol). We conclude that ADT is potentially explosive and must be treated with caution, being comparable to tosyl azide (TsN3). A maximum recommended process temperature for ADT is 55 °C.
Files
| Filename | Size | Type | Description |
|---|---|---|---|
| ADT result 1.001 | 619KB | application/octet-stream | 1. ADT DSC Result 1 - TA Intruments Universal Analysis file |
| ADT result 1.xlsx | 887KB | application/vnd.openxmlformats-officedocument.spreadsheetml.sheet | 1. ADT DSC Result 1 - Exported raw data in spreadsheet |
| ADT result 2.001 | 618KB | application/octet-stream | 2. ADT DSC Result 2 - TA Intruments Universal Analysis file |
| ADT result 2.xlsx | 903KB | application/vnd.openxmlformats-officedocument.spreadsheetml.sheet | 2. ADT DSC Result 2 - Exported raw data in spreadsheet |
| ADT open crucible.001 | 658KB | application/octet-stream | 3. ADT DSC Open Crucible Result - TA Intruments Universal Analysis file |
| ADT open crucible result.xlsx | 891KB | application/vnd.openxmlformats-officedocument.spreadsheetml.sheet | 3. ADT DSC Open Crucible Result - Exported raw data in spreadsheet |
| ADT GSK result 1.xlsx | 15KB | application/vnd.openxmlformats-officedocument.spreadsheetml.sheet | 4. ADT GSK DSC Result 1 - Exported raw data in spreadsheet |
| ADT GSK result 2.xlsx | 15KB | application/vnd.openxmlformats-officedocument.spreadsheetml.sheet | 5. ADT GSK DSC Result 2 - Exported raw data in spreadsheet |
| ADT TGA-EGMS data.zip | 391KB | application/zip | 6. ADT TGA-EGMS raw data. Includes raw data and exported spreadsheet for TGA, raw data for selected EGMS cycles and spreadsheet containing EGMS data with constructed baseline EGMS and the EGMS during ADT decomposition. |
| ADT TGA-EGMS data.mnpub | 0 | chemical/x-mnpub | Mestrenova signature file for ADT TGA-EGMS data.zip |
| ADT characterisation data.zip | 1MB | application/zip | 7. Characterisation data for ADT. Includes raw and processed 1H and 13C NMR, IR plot and spectrum file. |
| ADT characterisation data.mnpub | 0 | chemical/x-mnpub | Mestrenova signature file for ADT characterisation data.zip |
Associated DOIs
| Current dataset ... | DOI | Description |
|---|---|---|
| References | 10.1021/acs.joc.9b00269 | Associated Publication |