Despite the widespread application of diboron reagents in Suzuki–Miyaura borylation reactions, the thermal stability of diboron compounds is poorly understood. Seven commonly used diboron reagents were selected to investigate their thermal stability using Differential Scanning Calorimetry (DSC). Tetrahydroxydiboron (BBA) was specifically chosen for comprehensive safety characterization, considering the high thermal risk identified during the DSC screening. The decomposition of BBA was further explored using DSC in conjunction with Advanced Thermokinetics Software (AKTS), as well as Accelerating Rate Calorimetry (ARC) and Differential Accelerating Rate Calorimetry (DARC). Key safety parameters, such as the temperature at which the time to the maximum rate is 24 h (TMR₂₄ and T_D24), were estimated. Consistent results for TMR₂₄ were obtained across various methods, affirming the reliability of these techniques in the kinetic analysis. DARC and ARC testing reveal an exceptionally rapid thermal runaway for BBA to the extent that the self-heating rate cannot be tracked within the instrument’s limits. Furthermore, BBA was found to be insensitive to impact or friction. This study presents the general methodology and specific findings for BBA, with the aim of providing industry guidance for conducting process safety assessment and ensuring the safe utilization of diboron reagents during process development and scale-up.

中文翻译：

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四羟基二硼的热稳定性


尽管二硼试剂在铃木-宫浦硼化反应中广泛应用，但人们对二硼化合物的热稳定性知之甚少。选择七种常用的二硼试剂，使用差示扫描量热法 (DSC) 研究其热稳定性。考虑到 DSC 筛选过程中发现的高热风险，专门选择四羟基二硼 (BBA) 进行全面的安全表征。使用 DSC 结合高级热动力学软件 (AKTS)、加速量热法 (ARC) 和差示加速量热法 (DARC) 进一步探索 BBA 的分解。估计了关键安全参数，例如达到最大速率的时间为 24 小时时的温度（TMR ₂₄ 和 T _D24 ）。通过各种方法获得了一致的 TMR ₂₄ 结果，证实了这些技术在动力学分析中的可靠性。 DARC 和 ARC 测试显示 BBA 的热失控异常迅速，以至于无法在仪器的限制范围内跟踪自加热速率。此外，BBA 对冲击或摩擦不敏感。本研究介绍了 BBA 的一般方法和具体研究结果，旨在为进行工艺安全评估并确保在工艺开发和放大过程中安全使用二硼试剂提供行业指导。