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Scalable Process for the Production of a Highly Energetic Bromoacetylene Building Block
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2018-09-13 00:00:00 , DOI: 10.1021/acs.oprd.8b00223
Philipp Kohler 1 , Mischa Schwaninger 2 , Alfred Stutz 3 , Reinhard Karge 1 , Stefan Abele 1
Affiliation  

3-(Bromoethynyl)azetidine is a highly energetic building block (decomposition energy up to −1800 J g–1) that was required in multikilogram quantities for the production of an API. The development of a four-step, fully telescoped, scalable sequence for its synthesis is described, along with a detailed safety study of the corresponding hydrochloride salt in order to determine the potential explosive properties and transport classification. A screen of counterions identified the (+)-camphorsulfonic acid salt as the most suitable form for mitigation of the energetic properties, as judged by differential scanning calorimetry (onset 182 °C, energy −876 J g–1). This case study demonstrates how a daunting chemical structure can be “tamed” by chemical process development, tuning of molecular properties, and thorough safety investigations.

中文翻译:

生产高能溴乙炔构件的可扩展方法

3-(溴乙炔基)氮杂环丁烷是一种高能积木(分解能高达-1800 J g –1),需要多千克量才能生产API。描述了其合成的四步全伸缩可扩展序列的开发,以及对相应盐酸盐的详细安全性研究,以确定潜在的爆炸特性和运输分类。通过差示扫描量热法(起始温度182°C,能量-876 J g –1)判断,抗衡离子筛选确定(+)-樟脑磺酸盐是最合适的形式,用于缓解高能性能。)。该案例研究表明,如何通过化学过程开发,分子性质调整和彻底的安全研究来“驯服”令人生畏的化学结构。
更新日期:2018-09-13
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