49669-22-9

Basic information

• Product Name: 6,6'-DIBROMO-2,2'-DIPYRIDYL
• Synonyms: 6,6'-DIBROMO-2,2'-DIPYRIDYL;6,6'-DibroMo-2,2'-bipyridyl;6,6'-dibroMo-2,2'-bipyridine 97%
• CAS NO: 49669-22-9
• Molecular Formula: C₁₀H₆Br₂N₂
• Molecular Weight: 313.98
• Product Categories: Heterocyclic Compounds;C9 to C46Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridines
• Mol File: 49669-22-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 220-223 °C(lit.)
• Boiling Point: 369.4±37.0 °C(Predicted)
• Flash Point: 177.2oC
• Appearance: /
• Density: 1.809g/cm3
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: -0.44±0.22(Predicted)
• CAS DataBase Reference: 6,6'-DIBROMO-2,2'-DIPYRIDYL(CAS DataBase Reference)
• NIST Chemistry Reference: 6,6'-DIBROMO-2,2'-DIPYRIDYL(49669-22-9)
• EPA Substance Registry System: 6,6'-DIBROMO-2,2'-DIPYRIDYL(49669-22-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 49669-22-9(Hazardous Substances Data)

Usage

Uses

6,6''-Dibromo-2,2''-bipyridine is used as a catalyst for the preparation of iodoesters through copper-catalyzed [2,3]-and [1,2]-rearrangements of diazoesters and allylic iodides.

Upstream product

• 109-04-6 2-bromo-pyridine 
• 153025-65-1 ethyl (4-tert-butyldimethylsilyloxyphenyl)glyoxylate 
• 626-05-1 2,6-Dibromopyridine 
• 161584-76-5 Bis(1-oxo-2-pyridyl)methoxy<4-((tert-butyldimethylsilyl)oxy)phenyl>methane 
• 366-18-7 [2,2]bipyridinyl 

Downstream Products

• 273216-87-8 [2,2']Bipyridinyl-6,6'-dicarboxylic acid bis-[((S)-2-chloro-1-phenyl-ethyl)-amide] 
• 273216-89-0 6,6'-Bis-((S)-4-phenyl-4,5-dihydro-oxazol-2-yl)-[2,2']bipyridinyl 
• 455317-78-9 6,6'-bis{1-[N-((1S)-2-hydroxy-1-benzyl-ethyl)]carbamoyl-1-methyl-ethyl}-[2,2']bipyridinyl 
• 455317-91-6 6,6'-bis{1-[N-((1S)-2-chloro-1-benzyl-ethyl)]carbamoyl-1-methyl-ethyl}-[2,2']bipyridinyl 
• 455317-85-8 6,6'-bis{1-[N-((1R)-2-hydroxy-1-phenyl-ethyl)]carbamoyl-1-methyl-ethyl}-[2,2']bipyridinyl 
• 455317-83-6 6,6'-bis{1-[N-((1S)-2-hydroxy-1-phenyl-ethyl)]carbamoyl-1-methyl-ethyl}-[2,2']bipyridinyl 
• 455317-97-2 6,6'-bis{1-[N-((1R)-2-chloro-1-phenyl-ethyl)]carbamoyl-1-methyl-ethyl}-[2,2']bipyridinyl 
• 455317-95-0 6,6'-bis{1-[N-((1S)-2-chloro-1-phenyl-ethyl)]carbamoyl-1-methyl-ethyl}-[2,2']bipyridinyl 
• 501371-01-3 6,6'-bis[(2-trimethylsilylethynylphenyl)ethynyl]-2,2'-bipyridine 
• 501371-02-4 6,6'-bis[(2-ethynylphenyl)ethynyl]-2,2'-bipyridine 
• 871842-59-0 C₅₀H₄₈N₆O₈P₄ 
• 871842-57-8 C₄₈H₃₈N₆O₆P₂ 
• 871842-68-1 bis-[6'-diethylphosphonate-2,2'-bipyridin-6-yl]phenylphosphine oxide 

Relevant articles and documents

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).

A novel one-pot synthesis of 6,6''-dibromo-2,2': 6'2''-terpyridine

Dibromo-2,2': 6'2''-terpyridine was obtained in a moderate yield by lithiation of four molar amounts of 2,6-dibromopyridine with butyllithium followed by treatment with phosphorus trichloride in diethyl ether.