473294
双（频哪醇合）二硼
99%
别名:
双戊酰二硼
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关于此项目
经验公式（希尔记法）:
C12H24B2O4
化学文摘社编号:
分子量:
253.94
MDL编号:
UNSPSC代码:
12352103
PubChem化学物质编号:
NACRES:
NA.22
方案
99%
表单
powder (or crystals)
mp
137-140 °C (lit.)
SMILES字符串
CC1(C)OB(OC1(C)C)B2OC(C)(C)C(C)(C)O2
InChI
1S/C12H24B2O4/c1-9(2)10(3,4)16-13(15-9)14-17-11(5,6)12(7,8)18-14/h1-8H3
InChI key
IPWKHHSGDUIRAH-UHFFFAOYSA-N
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一般描述
双频哪醇合二硼或(B2pin2)是有机合成中最常用的二硼烷试剂，因其在空气和湿气环境中具有高稳定性。它可在酸性条件下通过四(二甲氨基)二硼和频哪醇的反应合成。
应用
用于构造四甲基吡咯烷硝基氧支架，以通过 Suzuki 偶联反应合成顺磁性杂环化合物。
用于铂催化乙炔和烯烃顺式邻二硼化反应的试剂；也可用于钯催化芳香烃的硼化反应。
钯催化 1,6-烯炔环化生成高烯丙基烷基硼酸酯的新型反应的底物。
储存分类代码
11 - Combustible Solids
WGK
WGK 3
闪点(°F)
Not applicable
闪点(°C)
Not applicable
个人防护装备
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Xu C, et al.
Transition Metal Chemistry, 34(2), 175-179 (2009)
Ronald L Reyes et al.
Science (New York, N.Y.), 369(6506), 970-974 (2020-08-21)
Site selectivity and stereocontrol remain major challenges in C-H bond functionalization chemistry, especially in linear aliphatic saturated hydrocarbon scaffolds. We report the highly enantioselective and site-selective catalytic borylation of remote C(sp3)-H bonds γ to the carbonyl group in aliphatic secondary
Synthesis, 2573-2573 (2006)
Pd-catalyzed borylative cyclization of 1,6-enynes.
Juan Marco-Martínez et al.
Journal of the American Chemical Society, 129(7), 1874-1875 (2007-01-31)
商品
Arylboronic acids and esters, vital tools in chemical transformations, find extensive use, particularly in the Suzuki-Miyaura cross-coupling reaction.
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