众所周知，叠氮化合物因其爆炸性著称，叠氮化铅、叠氮化银是著名的军工产品。而点击化学的“明星反应”CuAAC反应，却需要叠氮基团和末端炔基团作为分子砌块。
近期，Michael等人制备了卤代叠氮苯，并对其进行了差示扫描量热法（DSC）和冲击敏感性测试——后者即使用锤子“抡”在样品上，测试其安全性。
他们发现部分有机叠氮化合物对冲击十分敏感，因此，使用点击化学的叠氮砌块的时候，应特别注意安全。
论文链接：
Structural and Thermal Characterization of Halogenated Azidopyridines: Under-Reported Synthons for Medicinal Chemistry
机翻摘要：
由于参与了点击反应，双功能叠氮化物是制备药物和生化工具化合物的宝贵中间体。尽管吡啶类化合物在药物支架中具有优越性，但文献中几乎完全没有关于带有卤素取代基的叠氮类化合物的合成和表征的报道，以供进一步阐述。由于叠氮吡啶的氮原子和碳原子数量几乎相等，我们推测安全问题限制了这些有用的双功能构件在药物和生物化学中的应用。为了解决这个问题，我们制备并表征了9种含有单个氟、氯或溴原子的叠氮吡啶。所有这些都通过差示扫描量热法（DSC）进行了检测，其中它们显示了228-326 kJ/mol的放热，起始温度在119-135℃之间。选定的叠氮吡啶被推进到机械应力测试中，其中注意到C5H3FN4的一个再生异构体的冲击敏感性。通过在各种点击反应中的使用和卤素手柄的多样化，证明了这些多功能的中间体的效用。
摘要原文：
Owing to their participation in Click reactions, bifunctional azides are valuable intermediates in the preparation of medicines and biochemical tool compounds. Despite the privileged nature of pyridines among pharmaceutical scaffolds, reports of the synthesis and characterization of azidopyridines bearing a halogen substituent for further elaboration are almost completely unknown in the literature. As azidopyridines carry nearly equal numbers of nitrogen and carbon atoms, we hypothesized that safety concerns limited the application of these useful bifunctional building blocks in medicinal and biological chemistry. To address this concern, we prepared and characterized nine azidopyridines bearing a single fluorine, chlorine, or bromine atom. All were examined by differential scanning calorimetry (DSC), in which they demonstrated exotherms of 228–326 kJ/mol and onset temperatures between 119 and 135 °C. Selected azidopyridines were advanced to mechanical stress testing, in which impact sensitivity was noted for one regioisomer of C5H3FN4. The utility of these versatile intermediates was demonstrated through their use in a variety of Click reactions and the diversification of the halogen handles.
x-mol报道：
“点击化学”的叠氮吡啶试剂安不安全？实锤来了