2,2'-联吡啶-5,5'-二羧酸
| 中文名称 | 2,2'-联吡啶-5,5'-二羧酸 |
|---|---|
| 中文同义词 | 5,5'-二羧酸-2,2'-联吡啶;2,2-联吡啶-5,5-二羧酸 5G;2,2 -二吡啶-5,5 -二羧酸;2,2'-联吡啶-5,5‘-二甲酸;2,2'-联二吡啶-5,5'-二羧酸;2，2-联吡啶-5,5-二羧酸;6,6'-二烟酸;5,5-二羧基-2,2-联吡啶 |
| 英文名称 | 2,2'-Bipyridine-5,5'-dicarboxylic acid |
| 英文同义词 | 5,5'-Dicarboxy-2,2'-bipyridine;2,2''-BIPYRIDINE-5,5''-DICARBOXYLIC ACID 97%;2,2'-Bipyridine-5,5'-dicarboxylic acid;6-(5-carboxy-2-pyridyl)nicotinic acid;6-(5-carboxypyridin-2-yl)pyridine-3-carboxylic acid;2,2Bipyridyl-5,5'-dicarboxylic acid;2,2′-Bipyridine-5,5′-dicarboxylic acid, >=99%;Nicotinic EP Impurity B |
| CAS号 | 1802-30-8 |
| 分子式 | C12H8N2O4 |
| 分子量 | 244.2 |
| EINECS号 | 626-338-4 |
| 相关类别 | 通用试剂;羧酸;有机化工中间体、电子材料类产品;联吡啶;联吡啶羧酸类;生化试剂;有机砌块;医药中间体;pyridine;吡啶;C9 to C46;Heterocyclic Building Blocks;Pyridines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;中药对照品;2,2'-联吡啶;有机化学;化工原料;羧酸配体;API intermediates;Nicotine Derivatives;Pharmaceuticals;Heterocycle-Pyridine series |
| Mol文件 | 1802-30-8.mol |
| 结构式 |  |
2,2'-联吡啶-5,5'-二羧酸 性质
| 熔点 | >360 °C(lit.) |
|---|---|
| 沸点 | 521.0±50.0 °C(Predicted) |
| 密度 | 1.469±0.06 g/cm3(Predicted) |
| 储存条件 | Sealed in dry,Room Temperature |
| 溶解度 | DMSO（非常轻微，加热） |
| 形态 | 固体 |
| 酸度系数(pKa) | 1.95±0.10(Predicted) |
| 颜色 | 米白色 |
| InChI | InChI=1S/C12H8N2O4/c15-11(16)7-1-3-9(13-5-7)10-4-2-8(6-14-10)12(17)18/h1-6H,(H,15,16)(H,17,18) |
| InChIKey | KVQMUHHSWICEIH-UHFFFAOYSA-N |
| SMILES | C1(C2=NC=C(C(O)=O)C=C2)=NC=C(C(O)=O)C=C1 |
| CAS 数据库 | 1802-30-8(CAS DataBase Reference) |
可作为配体用于合成MOF材料，如:MOF-253;ZrMOF-BIPY/MOF-867
[2] Doping Metal-Organic Frameworks for Water Oxidation, Carbon Dioxide Reduction, and Organic Photocatalysis. https://doi.org/10.1021/ja203564w
[3] Metal Insertion in a Microporous Metal-Organic Framework Lined with 2,2'-Bipyridine. https://doi.org/10.1021/ja106935d
[4] Stability and degradation mechanisms of metal-organic frameworks containing the Zr6O4(OH)4 secondary building unit. https://doi.org/10.1039/c3ta10662d
[5] Supercapacitors of Nanocrystalline Metal-Organic Frameworks. https://doi.org/10.1021/nn5027092
2,2'-联吡啶-5,5'-二羧酸是一种烟酸衍生物，用于治疗高胆固醇血症、高脂血症和心血管疾病。它也用于医药中间体。
生产方法
1762-34-1
1802-30-8
以5,5'-二甲基-2,2'-联吡啶为原料合成2,2'-联吡啶-5,5'-二羧酸的一般步骤如下：将5,5'-二甲基-2,2'-联吡啶（1.0g）溶于水（35ml）中，加入高锰酸钾（KMnO4，6.0g）。将反应混合物在磁力搅拌下回流过夜。通过薄层色谱（TLC）监测反应进程，确认原料完全消耗后，过滤反应混合物以除去生成的二氧化锰（MnO2）。将滤液浓缩至约5毫升。随后，用35%的盐酸水溶液酸化浓缩液，并将混合物置于冰箱中过夜。通过过滤收集析出的白色沉淀，并用水多次洗涤，最终得到2,2'-联吡啶-5,5'-二羧酸（1.0g，产率74%）为白色粉末。
参考文献：
[1] Dalton Transactions, 2008, # 15, p. 2054 - 2060
[2] Journal of the American Chemical Society, 2012, vol. 134, # 2, p. 968 - 978
[3] Chemistry - A European Journal, 2012, vol. 18, # 23, p. 7030 - 7035
[4] Chemistry - A European Journal, 2013, vol. 19, # 40, p. 13369 - 13375
[5] Dalton Transactions, 2016, vol. 45, # 3, p. 881 - 885
参考文献
[1] Synthesis and Self-Inclusion of Bipyridine-Spaced Cyclodextrin Dimers. https://doi.org/10.1021/jo0256641
[2] Doping Metal-Organic Frameworks for Water Oxidation, Carbon Dioxide Reduction, and Organic Photocatalysis. https://doi.org/10.1021/ja203564w
[3] Metal Insertion in a Microporous Metal-Organic Framework Lined with 2,2'-Bipyridine. https://doi.org/10.1021/ja106935d
[4] Stability and degradation mechanisms of metal-organic frameworks containing the Zr6O4(OH)4 secondary building unit. https://doi.org/10.1039/c3ta10662d
[5] Supercapacitors of Nanocrystalline Metal-Organic Frameworks. https://doi.org/10.1021/nn5027092