Diazo-Transfer Reagent 2-Azido-4,6-dimethoxy-1,3,5-triazine Displays Highly Exothermic Decomposition Comparable to Tosyl Azide

被引：15

作者：

Green, Sebastian P. ^{[1
,2
]}

Payne, Andrew D. ^{[3
]}

Wheelhouse, Katherine M. ^{[4
]}

Hallett, Jason P. ^{[2
]}

Miller, Philip W. ^{[1
]}

Bull, James A. ^{[1
]}

机构：

[1] Imperial Coll London, Mol Sci Res Hub, Dept Chem, White City Campus,80 Wood Lane, London W12 0BZ, England

[2] Imperial Coll London, Dept Chem Engn, South Kensington Campus,Exhibit Rd, London SW7 2AZ, England

[3] GlaxoSmithKline, GSK Med Res Ctr, Pilot Plant Operat, Proc Safety, Gunnels Wood Rd, Stevenage SG1 2NY, Herts, England

[4] GlaxoSmithKline, GSK Med Res Ctr, Prod Dev & Supply, API Chem, Gunnels Wood Rd, Stevenage SG1 2NY, Herts, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 09期

基金：

英国工程与自然科学研究理事会;

关键词：

DIAZOTRANSFER; EFFICIENT;

D O I：

10.1021/acs.joc.9b00269

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 (T-init) of 159 degrees C and an enthalpy of decomposition (Delta H-D) 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 degrees C.

引用

页码：5893 / 5898

页数：6

共 29 条

[1]

[Anonymous], 2011, ORG LETT, V13, P2514

[2]

Banert K., 2010, Organic Azides: Syntheses and Applications

[3] DIAZOTRANSFER REACTIONS WITH PARA-ACETAMIDOBENZENESULFONYL AZIDE [J].