203573-76-6

Basic information

• Product Name: [2,2'-Bipyridine]-6-carboxylic acid, methyl ester
• Synonyms: [2,2'-Bipyridine]-6-carboxylic acid, methyl ester;Methyl 2,2'-bipyridine-6-carboxylate;[2,2'-Bipyridine]-6-carboxylic aci;Methyl 2,2-bipyridine-6-carboxylate: [2,2-Bipyridine]-6-carboxylic acid, methyl ester
• CAS NO: 203573-76-6
• Molecular Formula: C₁₂H₁₀N₂O₂
• Molecular Weight: 214.22
• Mol File: 203573-76-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [2,2'-Bipyridine]-6-carboxylic acid, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [2,2'-Bipyridine]-6-carboxylic acid, methyl ester(203573-76-6)
• EPA Substance Registry System: [2,2'-Bipyridine]-6-carboxylic acid, methyl ester(203573-76-6)

Safety Data

• Hazardous Substances Data: 203573-76-6(Hazardous Substances Data)

Usage

Description

[2,2'-Bipyridine]-6-carboxylic acid, methyl ester is a chemical compound with the molecular formula C13H11N2O2. It is a methyl ester derivative of 2,2'-Bipyridine-6-carboxylic acid, which is a bipyridine derivative commonly used in coordination chemistry and as a ligand in metal-catalyzed reactions. The methyl ester form of this compound adds a methyl group to the carboxylic acid functionality, making it more lipophilic and potentially improving its solubility in organic solvents.

Uses

Used in Chemical Research:
[2,2'-Bipyridine]-6-carboxylic acid, methyl ester is used as a research compound for its potential applications in chemical research, particularly in the field of coordination chemistry and metal-catalyzed reactions. Its unique structure and properties make it a valuable tool for studying various chemical processes and interactions.
Used in Organic Synthesis:
[2,2'-Bipyridine]-6-carboxylic acid, methyl ester is used as a synthetic building block in organic synthesis, where its lipophilic nature and improved solubility in organic solvents can be advantageous for the development of new compounds and materials.
Used in Pharmaceutical Industry:
[2,2'-Bipyridine]-6-carboxylic acid, methyl ester may have potential applications in the pharmaceutical industry, where its unique chemical properties could be harnessed for the development of new drugs or drug delivery systems. However, further research and development are necessary to explore its full potential in this field.
It is important to handle and use [2,2'-Bipyridine]-6-carboxylic acid, methyl ester with proper safety precautions, as it may have health hazards associated with its handling.

Upstream product

• 67-56-1 methanol 
• 4392-85-2 2,2'-bipyridyl-6-carbonitrile 
• 6636-55-1 methyl 6-chloropicolinate 
• 13737-05-8 2-trimethylstannylpyridine 
• 366-18-7 [2,2]bipyridinyl 
• 26218-75-7 methyl 6-Bromopicolinate 
• 882521-96-2 pyridine-2-boronic acid N-phenyldiethanolamine ester 
• 33421-43-1 2,2'-bipyridyl N-oxide 

Relevant articles and documents

Pyrene-appended bipyridine hydrazone ligand as a turn-on sensor for Cu2+ and its bioimaging application

A pyrene-appended bipyridine hydrazone-based ligand, HL, was synthesized and characterized by spectroscopic methods. Upon complexation with Cu(ii), HL formed a hexanuclear paddlewheel metal-organic macrocycle (MOM) via self-assembly with a high association constant with the molecular formula of [Cu6L6(NO3)6]. Intermolecular and intramolecular π-π interactions were demonstrated in this hexanuclear Cu(ii) complex. Further, it was observed that HL had the potential to detect a trace level of Cu(ii) ion selectively among a wide range of biologically relevant metal ions in aqueous medium at physiological pH. Using HL, it was feasible to sense copper(ii) ions in living cells due to its good cell permeability and high solubility under physiological conditions along with its high IC50 value. The low detection limit, high sensitivity and good reproducibility make this Cu-sensor very promising. The complex (MOM) formed between the ligand and Cu(ii) was found to be 1:1 on the basis of fluorescence titrations and was confirmed by ESI-MS. Moreover, single-crystal study of the hexanuclear self-assembled fluorescent species provided better insight into its chemistry, e.g. coordination environment and binding mode, unlike most of the metal sensors due to the lack of a single-crystal structure of the metal sensor complex. Cytotoxicity assay and bioimaging were performed in living cells (Vero cells), giving green fluorescent images. Fluorescence lifetime measurements and theoretical calculations were carried out. The morphology and topographic details on the surface of the metal-organic macrocycle (MOM) were studied by field-emission scanning electron microscopy (FESEM).

Synthesis of 2,2-Bipyridines via Suzuki-Miyaura Cross-Coupling

For a long time, the Suzuki-Miyaura cross-coupling reaction could not be used for the synthesis of 2,2′-bipyridines due to the lack of sufficiently stable 2-pyridylboron compounds. Stabilized 2-pyridylboronic acid esters recently developed by Hodgson, however, were found to be ideally suited for this purpose. Two general protocols could be developed and demonstrated to be valuable alternatives, which can be used very efficiently for the synthesis of functionalized 2,2-bipyridines.

Preparation of non-symmetrical 2,3-bis-(2,2'-oligopyridyl)pyrazines via 1,2-disubstituted ethanones

Sequential oxidation of the condensation products between alkyl 2,2'- oligopyridyl carboxylates and 6-methyl pyridine homologues with m-CPBA, then iodine affords the corresponding mixed α-diketones. These compounds are readily transformed into the respective mixed bis-oligopyridyl pyrazines, a class of compounds of interest for supramolecular chemistry.