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

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

Used in Chemical Synthesis:
5-METHYL-2,2'-BIPYRIDYL is used as an intermediate in the synthesis of metal-ion chelating amino acids for genetic incorporation into proteins. This application is significant in the development of biophysical probes, which are essential tools for studying the structure, function, and interactions of biological molecules.
Used in Biophysical Probes:
5-METHYL-2,2'-BIPYRIDYL is used as a component in the creation of biophysical probes for investigating the properties and behavior of proteins. These probes can help researchers understand the underlying mechanisms of various biological processes and may contribute to the development of new therapeutic strategies for diseases.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-METHYL-2,2'-BIPYRIDYL may be utilized in the development of new drugs or drug candidates, particularly those involving metal-ion chelating properties. Its unique structure and reactivity make it a valuable building block for designing novel therapeutic agents.
Used in Material Science:
5-METHYL-2,2'-BIPYRIDYL can also be employed in the field of material science, where its metal-ion chelating properties may be harnessed to develop new materials with specific properties, such as improved conductivity or enhanced stability.

Upstream product

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

Downstream Products

• 340130-54-3 (2R,3S)-1,3-Bis-benzyloxy-6-[2,2']bipyridinyl-5-yl-hexane-2,5-diol 
• 875634-83-6 (Z)-5-[4'-(2-biphenyl-4-yl-vinyl)-biphenyl-4-ylmethoxymethyl]-[2,2']bipyridine 
• 338800-85-4 (2R,3S,5R)-5-[2,2']Bipyridinyl-5-ylmethyl-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-ol 
• 340130-35-0 5-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-ylmethyl)-[2,2']bipyridinyl 
• 147323-44-2 1,3,5-tris<4-(((2,2'-bipyridyl-5-yl)carbonyl)benzylamino)methyl>benzene 
• 1262887-75-1 (2S,2'S)-tetra-tert-butyl 2,2'-((5-([2,2'-bipyridine]-5-carboxamido)isophthaloyl)bis(azanediyl))disuccinate 
• 1262887-76-2 di-tert-butyl (((5-([2,2'-bipyridine]-5-carboxamido)isophthaloyl)bis(azanediyl))bis(hexane-6,1-diyl))dicarbamate 
• 220339-96-8 5-(aminomethyl)-2,2′-bipyridine 
• 303050-47-7 [2,2'-bipyridin]-5-ylmethyl acetate 
• 179873-48-4 2,2’-bipyridine-5-carbaldehyde 
• 1443358-63-1 C₂₇H₃₄N₂O₂ 
• 1443358-83-5 C₂₅H₃₀N₂O₂ 
• 1443358-85-7 C₂₃H₂₆N₂O₂ 
• 1443358-53-9 C₅₁H₇₃BN₂O₅ 

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

Directed evolution using proteins comprising unnatural amino acids

The invention provides methods and compositions for screening polypeptide libraries that include variants comprising unnatural amino acids. In addition, the invention provides vector packaging systems and methods for packaging a nucleic acid in a vector. Compositions of vectors produced by the methods and systems are also provided.

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).

Heteroaryl cross-coupling as an entry toward the synthesis of lavendamycin analogues: A model study

(Chemical Equation Presented) ABC analogues of the antitumor antibiotic lavendamycin, which contain the key metal chelation site and redox-active quinone unit essential for biological activity, were prepared via the palladium(0)-catalyzed cross-coupling reaction of various 2-haloheteroaromatics with 2-stannylated pyridines and quinolines. Using the Stille reaction, 2-bromo substituted quinolines and 1-bromoisoquinolines were found to undergo efficient coupling with 2-pyridinylstannanes to provide unsymmetrical heterobiaryl derivatives. While the Stille reaction using the reverse coupling partners (i.e., 2-quinolinylstannanes and haloheteroaromatics) had not received much attention in the literature, we found that this alternative coupling reaction efficiently provided several new heterobiaryl derivatives. The gold-catalyzed intramolecular cycloisomerization of N-(prop-2-ynyl)-1H-indole-2-carboxamide smoothly afforded a β-carbolinone derivative that was subsequently used for a Pd(0)-catalyzed cross-coupling directed toward the synthesis of lavendamycin analogues.

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.

Functionalized 2,2′-bipyridines and 2,2′:6′,2″-terpyridines via stille-type cross-coupling procedures

Stille-type cross-coupling procedures are utilized in order to prepare a variety of functionalized 2,2′-bipyridines and 2,2′:6′,2″-terpyridines. Such N-heterocyclic compounds are of great interest as chelating ligands for transitionmetal ions in the field of supramolecular chemistry. Various mono- and disubstitued 2,2′-bipyridines were synthesized in high yields and multigram scales using a modular design principle. The terpyridines may be functionalized in one step with different substituents at the outer pyridine rings and at the 4′-position of the centered ring, leading to multifunctionalized compounds. The initially obtained methyl ester and ethyl ester groups can be simply converted into bromomethyl and hydroxymethyl groups which allow further functionalization reactions.

Stille-type cross-coupling - An efficient way to various symmetrically and unsymmetrically substituted methyl-bipyridines: Toward new ATRP catalysts

(matrix presented) Various mono- and disubstituted 2,2′-bipyridines were synthesized in high yields and multigram scales utilizing Stille-type coupling procedures. The corresponding bromo-picoline and tributyltin-picoline building blocks were prepared from commercially available amino-picoline compounds. As first examples of metal complexes, 4,5′-dimethyl-2,2′-bipyridine was reacted with copper(II) and iron(II) ions and investigated as catalyst in ATRP.