Scalable Process for the Production of a Highly Energetic Bromoacetylene Building Block,Organic Process Research & Development

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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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