4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane

• ChemBase编号: 8893
• 分子式: C12H24B2O4
• 平均质量: 253.93856
• 单一同位素质量: 254.18607005
• SMILES: B1(B2OC(C(O2)(C)C)(C)C)OC(C(O1)(C)C)(C)C
• Canonical SMILES: CC1(C)OB(OC1(C)C)B1OC(C(O1)(C)C)(C)C
• InChI: 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
• InChIKey: IPWKHHSGDUIRAH-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane
• IUPAC传统名: 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane; bis(pinacolato)diboron
• 别名: 双戊酰二硼; 双联频哪醇硼酸酯; 双戊酰二硼; Bis(pinacolato)diboron; 4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi-1,3,2-dioxaborolane; Bis(pinacolato)diboron; 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bis(1,3,2-dioxaborolane); 4,4',5,5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane; B2Pin2; Bis(pinacolate)diboron; Bis(pinacolato) diborate; Bis(pinacolato)diborane; Diboron Pinacol Ester; Dipinacoldiboron; Pinacol Diborane; 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane; Bis(pinacolato)diboron 99%; 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane; Bis(Pinacolato)diborane

登记号

• CAS号: 73183-34-3
• MDL号: MFCD00799570
• Beilstein号: 7703552
• PubChem SID: 160972200; 24870893
• PubChem CID: 2733548
• Chemspider ID: 2015334
• 维基百科标题: Bis(pinacolato)diboron

理论计算性质

• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 4.5764
• LogD (pH = 7.4): 4.5764
• Log P: 4.5764
• 摩尔折射率: 60.4776 cm^3
• 极化性: 28.11265 Å^3
• 极化表面积: 36.92 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; Methanol
• 外观: White Solid
• 熔点: 133-139°C; 137 - 140°C; 137-140 °C; 137-140 °C(lit.); 137-140°C; 139-141°C; ca 135°C
• 疏水性(logP): 3.106

安全信息

• 保存条件: Refrigerator, Under Inert Atmosphere
• 保存注意事项: Irritant; IRRITANT, IRRITANT-HARMFUL, KEEP COLD
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-37/39-60
• TSCA收录: false; 否
• GHS危险品标识: GHS07
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: 95%; 96%; 98+%; 99%
• Empirical Formula (Hill Notation): C12H24B2O4

详细说明

Apollo Scientific Ltd - OR5456

Versatile reagent for the preparation of boronic esters:J.Org.Chem.1995, 60,7508-7510.

Sigma Aldrich - 473294

Application
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。1
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。
包装
1, 5, 25 g in glass bottle
100 g in poly bottle
500 g in glass bottle

Toronto Research Chemicals - B522770

Bis(pinacolato)diboron is used as a condensation agent in the preparation poly(arylene)s. Bis(pinacolato)diboron is an organoboranate with potential use as matrix metallo-proteinase (MMP-2) inhibitor.

参考文献

• Ali, H.A. et al.: Arch. Pharm., 337, 183 (2004)
• Izumi, A. et al.: Chem. Lett., 7, 728 (2004)