4433-01-6

Basic information

• Product Name: 2,2'-Bipyridine-3,3'-dicarboxylic acid
• Synonyms: 2,2'-Bipyridine-3,3'-dicarboxylic acid;2'-Bipyridyl-3,3'-dicarboxylic acid;2,2Bipyridyl-3,3'-dicarboxylic acid;2,2'-Binicotinic Acid;3,3'-bis(hydroxycarbonyl)-2,2'-bipyridine
• CAS NO: 4433-01-6
• Molecular Formula: C12H8N2O4
• Molecular Weight: 244.2
• EINECS: 1312995-182-4
• Product Categories: Heterocyclic Compounds;C9 to C46;Heterocyclic Building Blocks;Pyridines
• Mol File: 4433-01-6.mol
• Article Data: 17

Chemical Properties

• Melting Point: 261°C(dec.)(lit.)
• Boiling Point: 454.1±40.0 °C at 760 mmHg
• Flash Point: 228.5±27.3 °C
• Appearance: /
• Density: 1.5±0.1 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 1.40±0.36(Predicted)
• CAS DataBase Reference: 2,2'-Bipyridine-3,3'-dicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Bipyridine-3,3'-dicarboxylic acid(4433-01-6)
• EPA Substance Registry System: 2,2'-Bipyridine-3,3'-dicarboxylic acid(4433-01-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 4433-01-6(Hazardous Substances Data)

Usage

General Description

3,3'-Dicarboxylic acid-2,2'-bipyridine is a chemical compound with the molecular formula C14H10N2O4. It is a bipyridine derivative with carboxylic acid groups attached to the 3 and 3' positions of the bipyridine ring. 2,2'-Bipyridine-3,3'-dicarboxylic acid has applications in coordination chemistry and as a ligand in various metal-catalyzed reactions. It is often used in the synthesis of coordination polymers and metal-organic frameworks due to its ability to coordinate with metal ions. Additionally, it has been studied for its potential use in developing luminescent materials and as a building block in molecular self-assembly.

Upstream product

• 66-71-7 1,10-Phenanthroline 
• 27318-90-7 1,10-phenanthroline-5,6-dione 
• 136869-49-3 3,3′-dicyano-2,2′-bipyridine 
• 41673-52-3 tris(1,10-phenanthroline)ruthenium(III)⁽³⁺⁾ 
• 2942-59-8 2-chloronicotinic acid 

Downstream Products

• 1762-36-3 3,3'-bis(ethoxycarbonyl)-2,2'-bipyridine 
• 1163299-59-9 bis[(2R,5S)-5-methyl-2-(1-methylethyl)cyclohexyl] 2,2'-bipyridine-3,3'-dicarboxylate 
• 71353-94-1 3,3'-Bis(hydroxymethyl)-2,2'-bipyridine 

Relevant articles and documents

Synthesis of new macrocycles with 2,2′-bipyridyl and polyamine functions

A series of macrocycles with two different complexing sites of the type 3,3′-AA-2,2′-bipyridine, where AA=CONHCH2CH 2NHCO, CONH(CH2)6NHCO, CONHCH 2CH2NHCH2CH2NHCO and CONHCH 2CH2CH2NHCH2CH2CH 2NHCO have been synthesized by high dilution method and characterized on the basis of elemental analysis, NMR, and infrared spectral data.

Spectrophotometric study of selective binding behaviors of dye molecules by pyridine-and bipyridine-modified ?2-cyclodextrin derivatives with a functional tether in aqueous solution

Four ?2-cyclodextrin (?2-CD) derivatives bearing pyridine or bipyridine linkers, i.e., mono[6-(3-pyridinecarboxamide)ethyleneamino-6-deoxy]-?2-CD(2), mono[6-(4-pyridinecarboxamide)ethyleneamino-6-deoxy]-?2-CD (3), N,Na?2-bis(2-aminoethyl)-2,2a?2-bipyridine-4, 4a?2-dicarboxamide-bridged bis(6-amino-6-deoxy-?2-CD) (4), N,Na?2-bis(2-aminoethyl)-2,2a?2-bipyridine-3, 3a?2-dicarboxamide-bridged bis(6-amino-6-deoxy-?2-CD) (5), and their copper-(II) complexes (6 and 7) were selected as molecular receptors to explore the conformation-function relationship of oligo(?2-CD)s. The original conformations of hosts 4-7 and their inclusion complexation behaviors with some guest molecules, i.e., ammonium 8-anilino-1-naphthalenesulfonate (ANS), sodium 6-(p-toludino)-2-naphthalenesulfonate (TNS), and rhodamine B (RhB), were comprehensively investigated by means of UV-vis, 2D NMR, and fluorescence spectroscopy. The results indicated that these oligo(?2-CD)s, especially bis(?2-CD) 5 and its copper(II) complex 7, exhibited the significantly enhanced binding abilities toward guest molecules as compared with native ?2-CD. Typically, hosts 5 and 7 efficiently enhanced the original binding ability of native ?2-CD toward ANS by a factor of 38-42 times. These increased binding abilities of oligomeric hosts were discussed from the viewpoint of the size/shape-fit and multipoint recognition between host and guest.

Correlation between the Structure and Catalytic Activity of [Cp*Rh(Substituted Bipyridine)] Complexes for NADH Regeneration

A series of water-soluble half-sandwich [Cp*RhIII(N^N)Cl]+ (Cp* = pentamethylcyclopentadiene, N^N-substituted 2,2′-bipyridine) complexes containing electron-donating substituents around the 2,2′-bipyridyl ligand were synthesized and fully characterized for the regioselective reduction of nicotinamide coenzyme (NAD+). The influence of the positional effect of the substituents on the structural, electrochemical, and catalytic properties of the catalyst was systematically studied in detail. The catalytic efficiency of the substituted bipyridine Cp*RhIII complexes are inversely correlated with their redox potentials. The 5,5′-substituted bipyridine Cp*RhIII complex, which had the lowest reduction potential, most effectively regenerated NADH with a turnover frequency of 1100 h-1. Detailed kinetic studies on the generation of intermediate(s) provide valuable mechanistic insight into this catalytic cycle and help to direct the future design strategy of corresponding catalysts.

D-π-A dye sensitizers made of polymeric metal complexes containing 1,10-phenanthroline and alkylfluorene or alkoxybenzene: Synthesis, characterization and photovoltaic performance for dye-sensitized solar cells

Four polymeric metal complexes (P1-P4 based on 1,10-phenanthroline metal complexes and alkylfluorene or alkoxybenzene were synthesized by the Heck coupling reaction and were developed for dye-sensitized solar cell applications. The target dyes use alkoxyb