53344-72-2

Usage

Uses

Used in Coordination Chemistry Research:
6,6'-Dichloro-2,2'-bipyridine is used as a building block for the synthesis of coordination complexes and metal-organic frameworks. Its ability to form stable complexes with transition metal ions makes it a valuable tool in this field.
Used in Catalysts:
6,6'-Dichloro-2,2'-bipyridine has been studied for its potential use in catalysis, where its unique properties can contribute to the development of new and efficient catalytic systems.
Used in Organic Electronics:
6,6'-Dichloro-2,2'-bipyridine has also been explored for its potential applications in organic electronics, where its properties may be harnessed to improve the performance of electronic devices.
Used in Chemical Synthesis:
6,6'-Dichloro-2,2'-bipyridine serves as a key intermediate in the synthesis of various organic compounds and pharmaceuticals, contributing to the development of new chemical entities with potential applications in medicine and other industries.

Upstream product

• 7275-43-6 [2,2']bipyridinyl 1,1'-dioxide 
• 21948-80-1 methyl 2-quinolyl sulfoxide 
• 87512-28-5 2-chloro-6-methylsulfinyl pyridine 
• 2402-78-0 2,6-dichloropyridine 
• 201230-82-2 carbon monoxide 
• 98-80-6 phenylboronic acid 
• 18412-57-2 p-tolyltriethoxysilane 
• 258506-66-0 2-chloro-5-iodo-pyridine 

Downstream Products

• 64741-33-9 [2,2'-bipyridine]-6,6'-diylbis(diphenylphosphine oxide) 

Relevant academic research and scientific papers

Copper-catalyzed Hiyama coupling of (hetero)aryltriethoxysilanes with (hetero)aryl iodides

A CuI-catalyzed Hiyama coupling was achieved, which proceeds in the absence of an ancillary ligand for aryl-heteroaryl and heteroaryl-heteroaryl couplings. A P,N-ligand is required to obtain the best product yields for aryl-aryl couplings. In addition to facilitating transmetalation, CsF is also found to function as a stabilizer of the [CuAr] species, potentially generated as an intermediate after transmetalation of aryltriethoxysilanes with Cu I-catalysts in the absence of ancillary ligands.

Electrochemical coupling of mono and dihalopyridines catalyzed by nickel complex in undivided cell

One step nickel-catalyzed electroreductive homocoupling among 2-bromopicolines and 2-bromopyridine has been investigated by our group in an undivided cell and using zinc or iron as sacrificial anode. In this work, it was developed mono and dihalopyridines coupling to obtain possible products from heterocoupling. A series of reactions were carried out in order to develop a synthetic method for the preparation of unsymmetrical 2,2′-bipyridines and 2,2′:6′,2″-terpyridines. Statistical yields (50%) were observed for 2-bromopyridines/2-bromo-6-methylpyridine heterocoupling. In a preliminary study devoted to terpyridines preparation, good results were obtained for 2,6-dihalopyridines homocoupling, affording 2,6-dichloro-2, 2′-bipyridine (46%) and 2,6-dibromo-2,2′-bipyridine (56%), at controlled reaction time. At major reaction time, it was observed that the direct electroreduction of the 2,6′-dihalo-2,2′-bipyridines intermediates and 2,6″-dihalo-2,2′:6′,2″-terpyridines products on the cathode surface. A reasonable isolated product yield of 6,6″-dimethyl-2,2′:6′,2″-terpyridine (10%) was only observed in the reaction between 2,6-dichloropyridine and 2-bromo-6- methylpyridine (1:2).

Palladium-catalyzed carbonylative coupling of pyridine halides with aryl boronic acids

The carbonylative Suzuki cross-coupling of a variety of mono-iodopyridines and bromopyridines (1a,b, 3a-c, 5) catalyzed by palladium-phosphane systems has been studied to prepare benzoylpyridine derivatives (2, 4, 6). The selectivity and the rate of the reaction are highly dependent on the reaction conditions, i.e. nature of the palladium catalyst precursor, solvent, temperature and CO pressure. The main side-products arise from direct, non-carbonylative cross-coupling. Under optimized conditions, benzoylpyridines are recovered in high yields (80-95%). The order of reactivity decreases from iodo- to bromopyridines and from 2-, 4- to 3-substituted halopyridines. The reactivity of dihalopyridines has been investigated; 2,6-dibromopyridine (7) and 3,5-dibromopyridine (11) are selectively transformed into either the corresponding benzoyl-phenylpyridine (8, 12) or the corresponding dibenzoylpyridine (9, 13). Dissymmetric 2,5-dihalopyridines (15a,b) are transformed into 2-benzoyl-5-bromopyridine (16) or 2,5-dibenzoylpyridine (17) in high yields.

A NOVEL REARRANGEMENT OF 2,2'-BIPYRIDINE N,N'-DIOXIDES THE CHARACTERISATION OF DIPYRIDO ISOXAZOLINIUM SALTS AS INTERMEDIATES IN THE FORMATION OF 3-HYDROXY-2,2'-BIPYRIDINES

The reactions of 2,2'-bipyridine N,N'-dioxides with POCl3 and SO2Cl2 have been investigated, and the products shown to be synthetically useful halogenated derivatives.The presence of substituents in the 4 position favours an intramolecular cyclisation to form dipyrido-isoxazolinium salts, which have been characterised for the first time.