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Product Code B1411-5g
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A frequent bipyridyl ligand with dicarboxylic acid anchoring groups

As the building block for the synthesis of organometallic compounds and the dicarboxylic acid anchoring groups are key functional groups to form 3D metal-organic frameworks (MOF)

2,2'-Bipyridine-5,5'-dicarboxylic acid, an isomer to 2,2'-bipyridine-4,4'-dicarboxylic acid, is another bipyridyl structure with dicarboxylic acid anchoring groups at 5,-5'-postions. It is one of the most frequently used heterocyclic building blocks in the synthesis of organometallic compounds and the dicarboxylic acid anchoring groups are key functional groups to form 3D metal-organic frameworks (MOF) which find application in carbon dioxide reduction, organic photocatalysis, water oxidation, antioxidants and lithium- and sodium-ion batteries.

Due to the highly ordered stacking structure of 2,2′-bipyridine-5,5′-dicarboxylic acid (H2bpy) imposed by hydrogen bonding, 2,2′-bipyridine-5,5′-dicarboxylic acid can be employed as anode material showing high specific capacity, good cycle stability, and remarkable rate performance in both lithium and sodium-ion batteries. 2,2′-bipyridine-5,5′-dicarboxylic acid has been reported to possess an ultrahigh initial capacity of lithium-ion battery of 1200 mAh•g-1 at a current density of 200 mA•g-1, and the specific capacity can maintain 550 mAh•g-1 after 100 cycles.

Using 2,2'-bipyridine-5,5'-dicarboxylic acid as the binding ligand, both RuH(H2bpy)(PPh3)2(CO)] (I) and [RuH(H2bpy)(AsPh3)2(CO)] (II) shows excellent radical scavenging properties as potential cancer treating agents with less toxicity on normal cell NIH 3T3 and considerable cyto-toxic activity against HeLa and HepG2 cancer cell lines.

General Information

CAS Number 1802-30-8
Chemical Formula C12H8N2O4
Full Name 2,2′-Bipyridine-5,5′-dicarboxylic acid
Molecular Weight 244.20 g/mol
Synonyms 5,5'-Dcbpy, 2,2′-Bipyridyl-5,5′-dicarboxylic acid, 6,6′-Binicotinic acid
Classification / Family Bipyridyl derivatives, Semiconductor synthesis intermediates, Dye-sensitized solar cells (DSSCs)

Chemical Structure

2,2′-Bipyridine-5,5′-dicarboxylic acid chemical structure, 1802-30-8
2,2′-Bipyridine-5,5′-dicarboxylic acid (5,5'-dcbpy), CAS 1802-30-8

Product Details

Purity >98% (1H NMR)
Melting Point >365 °C
Appearance White off-white to orange powder/crystals

MSDS Documentation

2,2′-bipyridine-5,5′-dicarboxylic acid2,2′-Bipyridine-5,5′-dicarboxylic acid MSDS Sheet

Literature and Reviews

  1. Bipyridine carboxylic acid as a high-performance anode material for lithium- and sodium-ion batteries, Y. Bo et al., Electrochim. Acta, 405, 139628 (2022); DOI: 10.1016/j.electacta.2021.139628.
  2. Cationic Zr-based metal-organic framework via post-synthetic alkylation for selective adsorption and separation of anionic dyes, J. Liu et al., Mater. Today Chem., 24, 100897 (2022); DOI: 10.1016/j.mtchem.2022.100897.
  3. Protection Against Cu(II)-Induced Oxidative Stress and Toxicity to Chlorella vulgaris by 2,2′-Bipyridine-5,5′-dicarboxylic Acid, Y. Wen et al., Arch. Environ. Contam. Toxicol. 66, 400–406 (2014); DOI: 10.1007/s00244-013-9977-2
  4. Synthesis and Properties of Polyamides and Polyesters On the basis of 2,2‘-Bipyridine-5,5‘-Dicarboxylic Acid and the Corresponding Polymer−Ruthenium Complexes, S. Yu et al., Macromolecules, 33 (9), 3259–3273 (2000); DOI: 10.1021/ma991863j.
  5. Ruthenium(II) complexes of 2,2′-bipyridine-5,5′-dicarboxylic acid: Synthesis, structure, DNA binding, cytotoxicity and antioxidant activity, T. Kamatchi et al., Inorganica Chim. Acta, 404, 58-67 (2013); DOI: 10.1016/j.ica.2013.04.029.
  6. Cu2+-Modified Metal–Organic Framework Nanoparticles: A Peroxidase-Mimicking Nanoenzyme, W. Chen et al., Small, 14 (5), 1703149 (2018); DOI: 10.1002/smll.201703149.
  7. Nickel(II) and manganese(II) metal–organic networks driven by 2,2′-bipyridine-5,5′-dicarboxylate blocks: synthesis, structural features, and magnetic properties, G. Zhang et al., Transition Met Chem 41, 153–160 (2016); DOI: 10.1007/s11243-015-0007-2.
  8. Doping Metal–Organic Frameworks for Water Oxidation, Carbon Dioxide Reduction, and Organic Photocatalysis, C. Wang et al., J. Am. Chem. Soc., 133, 34, 13445–13454 (2011); DOI: 10.1021/ja203564w.
  9. Photoexcitationof Fe3O Nodesin MOFDrivesWaterOxidationat pH=1 WhenRu CatalystIs, R. Ezhov et al., hemSusChem, e202202124 (2023); DOI: 10.1002/cssc.202202124.

To the best of our knowledge the information provided here is accurate. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. Products may have minor cosmetic differences (e.g. to the branding) compared to the photos on our website. All products are for laboratory and research and development use only.

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