56100-20-0

Basic information

• Product Name: 5-METHYL-2,2'-BIPYRIDYL
• Synonyms: 5-METHYL-2,2'-BIPYRIDYL;5-Methyl-2,2'-bipyridine;5-methyl-2-pyridin-2-ylpyridine;5-Methyl-[2,2']bipyridinyl
• CAS NO: 56100-20-0
• Molecular Formula: C₁₁H₁₀N₂
• Molecular Weight: 170.21
• EINECS: 200-258-5
• Mol File: 56100-20-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 92 °C(Press: 0.05 Torr)
• Appearance: /
• Density: 1.081±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DCM
• PKA: 4.39±0.20(Predicted)
• CAS DataBase Reference: 5-METHYL-2,2'-BIPYRIDYL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYL-2,2'-BIPYRIDYL(56100-20-0)
• EPA Substance Registry System: 5-METHYL-2,2'-BIPYRIDYL(56100-20-0)

Safety Data

• Hazardous Substances Data: 56100-20-0(Hazardous Substances Data)

Usage

Uses

5-Methyl-2,2''-bipyridine is an intermediate in the synthesis of genetic incorporation of a metal-ion chelating amino acids into proteins as a biophysical probe.

Upstream product

• 109-04-6 2-bromo-pyridine 
• 3510-66-5 2-Bromo-5-methylpyridine 
• 109-09-1 2-chloropyridine 
• 17997-47-6 2-tri-n-butylstannylpyridine 

Downstream Products

• 875634-83-6 (Z)-5-[4'-(2-biphenyl-4-yl-vinyl)-biphenyl-4-ylmethoxymethyl]-[2,2']bipyridine 
• 303050-47-7 [2,2'-bipyridin]-5-ylmethyl acetate 
• 179873-48-4 2,2’-bipyridine-5-carbaldehyde 
• 220339-96-8 5-(aminomethyl)-2,2′-bipyridine 

Relevant articles and documents

Biosynthesis of a site-specific DNA cleaving protein

An E. coli catabolite activator protein (CAP) has been converted into a sequence-specific DNA cleaving protein by genetically introducing (2,2′-bipyridin-5-yl)alanine (Bpy-Ala) into the protein. The mutant CAP (CAP-K26Bpy-Ala) showed comparable binding affinity to CAP-WT for the consensus operator sequence. In the presence of Cu(II) and 3-mercaptopropionic acid, CAP-K26Bpy-Ala cleaves double-stranded DNA with high sequence specificity. This method should provide a useful tool for mapping the molecular details of protein-nucleic acid interactions. Copyright

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).

In situ formation and reaction of 2-pyridylboronic esters

2-Pyridylboronic esters were generated by cross-coupling 2-bromopyridines with bis(pinacolato)diboron in the presence of a base and palladium catalyst. The boronic esters reacted in situ with unreacted 2-bromopyridines to afford high yields of 2,2′-bipyridines as homocoupled products. Depending upon the reaction conditions, varying amounts of protodeboronated products were also observed. An attempted cross-coupling between two different 2-bromopyridines produced a nearly statistical mixture of homo- and cross-coupled products.