53344-72-2

Basic information

• Product Name: 6,6'-Dichloro-2,2'-bipyridine
• Synonyms: 2,2'-Bi(6-chloropyridine);6,6'-Dichloro-2,2'-bipyridine;2-chloro-6-(6-chloropyridin-2-yl)pyridine
• CAS NO: 53344-72-2
• Molecular Formula: C₁₀H₆Cl₂N₂
• Molecular Weight: 225.07
• Mol File: 53344-72-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 220℃ (benzene )
• Boiling Point: 354.7±37.0 °C(Predicted)
• Appearance: /
• Density: 1.363±0.06 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: -0.40±0.10(Predicted)
• CAS DataBase Reference: 6,6'-Dichloro-2,2'-bipyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 6,6'-Dichloro-2,2'-bipyridine(53344-72-2)
• EPA Substance Registry System: 6,6'-Dichloro-2,2'-bipyridine(53344-72-2)

Safety Data

• Hazardous Substances Data: 53344-72-2(Hazardous Substances Data)

Usage

General Description

6,6'-Dichloro-2,2'-bipyridine is a chemical compound that belongs to the class of bipyridine derivatives. It is a crystalline, yellow solid with a molecular formula of C10H6Cl2N2. 6,6'-Dichloro-2,2'-bipyridine is often used as a building block in the synthesis of coordination complexes and metal-organic frameworks. It has also been studied for its potential use in catalysis and organic electronics. 6,6'-Dichloro-2,2'-bipyridine is known for its ability to form stable complexes with transition metal ions, making it a valuable tool in coordination chemistry research. However, it is important to handle this compound with caution as it is toxic and should be used in a well-ventilated area with proper protective equipment.

Upstream product

• 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 
• 7275-43-6 [2,2']bipyridinyl 1,1'-dioxide 

Downstream Products

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

Relevant articles and documents

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.

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.