2,2'-Bipyridine-6,6'-dicarboxylic acid

Base Information

• Chemical Name: 2,2'-Bipyridine-6,6'-dicarboxylic acid
• CAS No.: 4479-74-7
• Molecular Formula: C12H8N2O4
• Molecular Weight: 244.207
• European Community (EC) Number: 806-930-0
• DSSTox Substance ID: DTXSID40433318
• Nikkaji Number: J803.136C
• Wikidata: Q72443919
• ChEMBL ID: CHEMBL3586255
• Mol file: 4479-74-7.mol

Synonyms:4479-74-7;2,2'-BIPYRIDINE-6,6'-DICARBOXYLIC ACID;[2,2'-Bipyridine]-6,6'-dicarboxylic acid;6-(6-carboxypyridin-2-yl)pyridine-2-carboxylic Acid;2,2-bipyridine-6,6-dicarboxylic acid;MFCD11042476;6,6'-Bipicolinic acid;SCHEMBL70765;YSWG070;CHEMBL3586255;DTXSID40433318;LT0041;2,2-bipyridine-6,6-dicarboxylicacid;AKOS022175262;CS-W004578;AS-63566;SY055473;B3533;FT-0708240;Y10555;A872465;W-202793;2,2 inverted exclamation mark -Bipyridine-6,6 inverted exclamation mark -dicarboxylic Acid;2,2-Bipyridine-6,6-dicarboxylic Acid

Chemical Property of 2,2'-Bipyridine-6,6'-dicarboxylic acid

Chemical Property:

• Melting Point: 286ºC
• Boiling Point: 568.1 °C at 760 mmHg
• PKA: 2.97±0.10(Predicted)
• Flash Point: 297.4 °C
• PSA: 100.38000
• Density: 1.469 g/cm³
• LogP: 1.54000
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 244.04840674
• Heavy Atom Count: 18
• Complexity: 302

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,2'-Bipyridine-6,6'-dicarboxylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=NC(=C1)C(=O)O)C2=NC(=CC=C2)C(=O)O

Technology Process of 2,2'-Bipyridine-6,6'-dicarboxylic acid

There total 11 articles about 2,2'-Bipyridine-6,6'-dicarboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2,2′-bipyridine-6,6′-dicarbonitrile (4411-83-0) → 2,2'-bipyridine-6,6'-dicarboxylic acid (4479-74-7)

Guidance literature:

With sulfuric acid; acetic acid; at 20 ℃;

DOI:10.1002/chem.200900912

Reference yield: 98.0%

6,6'-dimethyl-2,2'-bipyridine (4411-80-7) → 2,2'-bipyridine-6,6'-dicarboxylic acid (4479-74-7)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; at 35 ℃; Cooling with ice;

DOI:10.1002/chem.201000572

Reference yield: 96.0%

6,6′-bis(ethoxycarbonyl)-2,2′-bipyridine (65739-40-4) → 2,2'-bipyridine-6,6'-dicarboxylic acid (4479-74-7)

Guidance literature:

With sodium hydroxide; In ethanol; at 78 ℃; for 18h;

DOI:10.1002/ejoc.201601597

upstream raw materials:

6,6'-dimethyl-2,2'-bipyridine

2,2′-bipyridine-6,6′-dicarbonitrile

6,6'-Dibromo-2,2'-bipyridine

carbon dioxide

Downstream raw materials:

6,6′-bis(ethoxycarbonyl)-2,2′-bipyridine

[Ru^II(2,2′-bipyridine-6,6′-dicarboxylate)(4-[Ph(CH₂)₃]-pyridine)₂]

Refernces

• 1、 Buenzli, Jean-Claude G.,Charbonniere, Loic J.,Ziessel, Raymond F.. "Structural and photophysical properties of Lnin complexes with 2,2'-bipyridine-6,6'-dicarboxylic acid: Surprising formation of a H-bonded network of bimetallic entitiesf". . p. 1917 - 1923. Retrieved 2000.
• 2、 Adamo, F.,Alessio, E.,Iengo, E.,Vidal, A.. "Models of molecular photocatalysts for water oxidation: Strategies for conjugating the Ru(bda) fragment (bda = 2,2′-bipyridine-6,6′-dicarboxylate) to porphyrin photosensitizers". supporting information. . Retrieved 2020/12/09.
• 3、 Yamazaki, Shigekazu. "Chromium(VI) oxide-mediated oxidation of polyalkyl-polypyridines to polypyridine-polycarboxylic acids with periodic acid". supporting information. p. 2210 - 2218. Retrieved 2019/06/25.