2,2'-Bipyridine-5,5'-dicarboxylic acid

Base Information

• Chemical Name: 2,2'-Bipyridine-5,5'-dicarboxylic acid
• CAS No.: 1802-30-8
• Molecular Formula: C12H8N2O4
• Molecular Weight: 244.207
• Hs Code.: 29333990
• European Community (EC) Number: 626-338-4
• DSSTox Substance ID: DTXSID50170929
• Nikkaji Number: J566.538H
• Wikidata: Q72443915
• Pharos Ligand ID: 4HGHXAAMXJKY
• ChEMBL ID: CHEMBL332005
• Mol file: 1802-30-8.mol

Synonyms:(2,2'-bipyridine)-5,5'-dicarboxylic acid;2,2'-bipy-5,5'-diCOOH

Chemical Property of 2,2'-Bipyridine-5,5'-dicarboxylic acid

Chemical Property:

• Melting Point: >360 ºC(lit.)
• Boiling Point: 521 ºC at 760 mmHg
• PKA: 1.95±0.10(Predicted)
• Flash Point: 268.9 ºC
• PSA: 100.38000
• Density: 1.469 g/cm³
• LogP: 1.54000
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Very Slightly, Heated)
• XLogP3: 0.5
• 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%min ^*data from raw suppliers

2,2'-Bipyridine-5,5'-dicarboxylic Acid >98.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=NC=C1C(=O)O)C2=NC=C(C=C2)C(=O)O
• Description: 2,2''-Bipyridine-5,5''-dicarboxylic acid is a heterocyclic building block. It has been used in the synthesis of metal-organic frameworks for water oxidation, organic photocatalysis, and carbon dioxide reduction.
• Uses: A Nicotinic acid (N429250) derivative for treatment of hypercholesterolemia and hyperlipidemia and cardiovascular disease.

Technology Process of 2,2'-Bipyridine-5,5'-dicarboxylic acid

There total 16 articles about 2,2'-Bipyridine-5,5'-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: 98.0%

5,5'-dimethyl-2,2'-bipyridine (1762-34-1) → 2,2'-bipyridine-5,5'-dicarboxylic acid (1802-30-8)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; periodic acid; In water; at 20 ℃; for 24h;

DOI:10.1080/00397911.2019.1618875

Reference yield: 84.0%

6-Chloro-3-pyridinecarboxylic acid (5326-23-8) → 2,2'-bipyridine-5,5'-dicarboxylic acid (1802-30-8)

Guidance literature:

With hydrogenchloride; sodium hydroxide; palladium; In methanol; water;

Reference yield: 56.0%

[2,2']bipyridinyl-5,5'-dicarboxylic acid diethyl ester (1762-46-5) → 2,2'-bipyridine-5,5'-dicarboxylic acid (1802-30-8)

Guidance literature:

In ethanol; water; for 3h; Heating;

DOI:10.1021/jm00076a014

upstream raw materials:

nicotinic acid

5,5'-dimethyl-2,2'-bipyridine

[2,2']bipyridinyl-5,5'-dicarboxylic acid diethyl ester

3-Methylpyridine

Downstream raw materials:

[2,2']bipyridinyl-5,5'-dicarboxylic acid diethyl ester

5'-(ethoxycarbonyl)-2,2'-bipyridine-5-carboxylic acid

5,5'-(2,2'-bipyridine)diacid chloride

2,2′-bipyridine-5,5′-dicarbaldehyde

Refernces

• 1、 Lataifeh, Anas,Kraatz, Heinz-Bernhard,Awwadi, Firas F.,Zaitoun, Mohammed A.,Sakai, Ken. "Platinum(II)-glutamic acid dendrimer conjugates: Synthesis, characterization, DFT calculation, conformational analysis and catalytic properties". . p. 245 - 254. Retrieved 2018.
• 2、 Saha, Subrata,Santra, Saikat,Akhuli, Bidyut,Ghosh, Pradyut. "Rotaxane with multiple functional groups". . p. 11170 - 11178. Retrieved 2014.
• 3、 Lee, Taek Seung,Kim, Young-Shin,Kwon, Na Young,Kim, Dai Gun,Lee, Minjung. "Synthesis of conjugated polymer containing bipyridine and oxadiazole groups and its metal ion sensing property". . p. 43 - 53. Retrieved 2010.
• 4、 Ziyaev et al.. "-". . . Retrieved 1978.
• 5、 Nonaka, Yuki,Uruno, Ryuhei,Dai, Fumiko,Matsuoka, Ryoji,Nakamura, Masaki,Iwamura, Maho,Iwabuchi, Haruo,Okada, Takahiro,Chigira, Naoto,Amano, Yoshitsugu,Hasegawa, Teruaki. "Hexavalent glycoclusters having tris-bipyridine ferrous complex cores as minimum combinatorial libraries for probing carbohydrate–carbohydrate interactions". . p. 5456 - 5464. Retrieved 2016.
• 6、 Gómez-González, Jacobo,Pérez, Yolanda,Sciortino, Giuseppe,Roldan-Martín, Lorena,Martínez-Costas, José,Maréchal, Jean-Didier,Alfonso, Ignacio,Vázquez López, Miguel,Vázquez, M. Eugenio. "Dynamic Stereoselection of Peptide Helicates and Their Selective Labeling of DNA Replication Foci in Cells**". supporting information. p. 8859 - 8866. Retrieved 2021/02/01.
• 7、 Gaire, Sanjay,Schrage, Briana R.,Ziegler, Christopher J.. "An Organometallic Isostere of an Amino Acid". supporting information. p. 10105 - 10108. Retrieved 2021/07/28.