1762-32-9

Usage

Uses

Used in Coordination Chemistry:
3,3'-DIMETHYL-2,2'-BIPYRIDINE is used as a ligand for forming stable complexes with transition metal ions, which is crucial in various chemical and catalytic processes. Its ability to chelate metal ions enhances the stability and reactivity of the resulting complexes, making it a key component in this field.
Used in Organic Synthesis:
As a building block, 3,3'-DIMETHYL-2,2'-BIPYRIDINE is utilized in the preparation of a variety of functional materials. Its structural features allow for the creation of new organic compounds with specific properties, which can be tailored for use in different applications.
Used in Material Science:
3,3'-DIMETHYL-2,2'-BIPYRIDINE contributes to the development of advanced materials due to its unique properties. It is employed in the synthesis of materials with specific functions, such as in sensors, catalysts, or other specialized applications where its interaction with metal ions can be exploited.
Used in Academic Research:
3,3'-DIMETHYL-2,2'-BIPYRIDINE is a valuable component in academic research, where its properties are explored and expanded upon. It is used to study the fundamental aspects of coordination chemistry, as well as to develop new methodologies and applications in material science.
Used in Industrial Research:
In industrial applications, 3,3'-DIMETHYL-2,2'-BIPYRIDINE is employed for the development of new products and processes that leverage its ability to form stable complexes and its role in material synthesis. Its use in industrial research aids in the innovation of products with improved performance and functionality.

Upstream product

• 3430-17-9 2-bromo-3-picoline 
• 108-99-6 3-Methylpyridine 
• 7705-08-0 iron(III) chloride 
• 5707-04-0 Phenylselenyl chloride 
• 1603-40-3 3-methylpyridin-2-ylamine 
• 1003-56-1 3-methylpyridin-2-ol 
• 1279130-01-6 3-methyl-2-(p-tolylthio)pyridine 
• 5315-25-3 2-bromo-6-methylpyridine 

Downstream Products

• 71632-84-3 tetracarbonyl(3,3'-dimethyl-2,2'-bipyridine)tungsten⁽⁰⁾ 

Relevant academic research and scientific papers

Synthesis, Luminescence Quantum Yields, and Lifetimes of Trischelated Ruthenium(II) Mixed-ligand Complexes Including 3,3'-Dimethyl-2,2'-bipyridyl

New five complexes of the type of X2(x=1,2,3, L=2,2'-bipyridyl or 1,10-phenanthroline, dmby=3,3'-dimethyl-2,2'-bipyridyl, X=halide ion) have been synthesized in order to investigate the effects of two methyl groups of dmby on the absorption and emission spectra, luminescence quantum yields, and lifetimes.Values of the radiative and nonradiative rate constants have been calculated from these data at 77 K.Although the absorption and emission maxima and the lifetimes are not much affected by the dmby ligand substitution, the molar extinction coefficients and emission quantum yields are decreased compared with trischelated complexes of the parent bipyridyl or phenanthroline ligands.At 25 deg C the emission yields of the complexes containing dmby decrease by 3-4 orders of magnitude than at 77 K.Possible causes of the decrease in the quantum yields are discussed.

Influence of the torsion angle in 3,3′-Dimethyl-2,2′-bipyridine on the intermediate valence of Yb in (C5Me5) 2Yb(3,3′-Me2-bipy)

The synthesis and X-ray crystal structures of Cp*2Yb(3, 3′-Me2bipy) and [Cp*2Yb(3,3′-Me 2bipy)][Cp*2YbCl1.6I0.4] ·CH2Cl2 are described. In both complexes, the NCCN torsion angles are approximately 40. The temperature-independent value of n f of 0.17 shows that the valence of ytterbium in the neutral adduct is multiconfigurational, in reasonable agreement with a CASSCF calculation that yields a nf value of 0.27; that is, the two configurations in the wave function are f13(π*1)1 and f 14(π*1)0 in a ratio of 0.27:0.73, respectively, and the open-shell singlet lies 0.28 eV below the triplet state (nf accounts for f-hole occupancy; that is, nf = 1 when the configuration is f13 and nf = 0 when the configuration is f14). A correlation is outlined between the value of n f and the individual ytterbocene and bipyridine fragments such that, as the reduction potentials of the ytterbocene cation and the free x,x′-R2-bipy ligands approach each other, the value of n f and therefore the f13:f14 ratio reaches a maximum; conversely, the ratio is minimized as the disparity increases.

Synthesis of Pyridylsulfonium Salts and Their Application in the Formation of Functionalized Bipyridines

An S-selective arylation of pyridylsulfides with good functional group tolerance was developed. To demonstrate synthetic utility, the resulting pyridylsulfonium salts were used in a scalable transition-metal-free coupling protocol, yielding functionalized bipyridines with extensive functional group tolerance. This modular methodology permits selective introduction of functional groups from commercially available pyridyl halides, furnishing symmetrical and unsymmetrical 2,2′- A nd 2,3′-bipyridines. Iterative application of the methodology enabled the synthesis of a functionalized terpyridine with three different pyridine components.

Reductive couplings of 2-halopyridines without external ligand: Phosphine-free nickel-catalyzed synthesis of symmetrical and unsymmetrical 2,2'-bipyridines

An unexpectedly facile synthetic approach for symmetrical and unsymmetrical 2,2'-bipyridines through the Ni-catalyzed reductive couplings of 2-halopyridines was developed. The couplings were efficiently catalyzed by 5 mol % of NiCl2.6H2O without the use of external ligands. A variety of 2,2'-bipyridines including caerulomycin F have been efficiently synthesized.

Dilithium tetrachlorocuprate(II) catalyzed oxidative homocoupling of functionalized grignard reagents

An efficient procedure is described for the oxidative homocoupling of functionalized Grignard reagents using a catalytic amount of dilithium tetrachlorocuprate(II) (CuLi2Cl4) in the presence of pure oxygen gas. This method is applied successfully to a variety of aryl, heteroaryl, alkyl, alkenyl and alkynyl halides, which are converted into the corresponding homocoupled products in good to excellent yields. Georg Thieme Verlag Stuttgart · New York.

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).

Catalytic homocoupling of aryl, alkenyl, and alkynyl halides with Ni(II)-complexes and zirconocene dichloride

A new catalytic system (cat. (H)2Phen(Me)2· NiCl2 or (MeO)2Dipyr(H)2·NiCl 2, cat. Zr(cp)2Cl2, 2 equiv Mn, and 2 equiv LiCl) has been developed to facilitate the homocoupling of a wide range of aryl, alkenyl, and alkynyl halides.

NOVEL PYRIDINE OXIDE COMPOUND, AND PROCESS FOR PRODUCING CARBOXYLIC ACID DERIVATIVE AND OPTICALLY ACTIVE CARBOXYLIC ACID DERIVATIVE WITH THE USE OF THE SAME

The invention relates to a pyridine oxide compound represented by formula (I), an optically active compound thereof, a salt thereof and a hydrate thereof, and, in the presence of the compound as a catalyst, performing 1) a method for producing an ester compound or an amide compound from a carboxylic acid equivalent and an alcohol or an amine, 2) an asymmetric esterification reaction or 3) an asymmetric amidation reaction. In formula (I), each R1 may be the same as the other R1 or different and each R1 represents an alkyl group, an aromatic group, a heterocyclic group, a carboxyl group, an ester group, a cyano group, a halogen atom, an oxygen atom, a sulfur atom or a nitrogen atom; each R2 may be the same as the other R2 or different and each R2 represents a hydrogen atom, an alkyl group, an aromatic group, a heterocyclic group, a carboxyl group, an ester group, a cyano group, a halogen atom, an oxygen atom or the like, and R3 and R4 may be the same or different and R3 and R4 each represent a hydrogen atom, an alkyl group, an aromatic group, a heterocyclic group, a carboxyl group, an ester group, a cyano group, a halogen atom, an oxygen atom or the like.

Mixed effect of the supporting electrolyte and the zinc anode in the electrochemical homocoupling of 2-bromopyridines catalyzed by nickel complexes in an undivided cell

Nickel-catalyzed electroreductive homocoupling of 2-bromomethylpyridines and 2-bromopyridine has been investigated in an undivided cell in the presence of a zinc sacrificial anode. A series of reactions were performed with various types and concentrations of supporting electrolyte. It was observed that a key step in this process is the formation of an arylzinc through a nickel-zinc transmetalation. This intermediate can be transformed back to the reactive arylnickel species to afford the homocoupling as the final product. The back process from the arylzinc intermediate is, however, suppressed in the presence of high concentration (0.2 M) of tetraalkylammonium salts. On the contrary, with NaI, the formation of the dimer is not prevented, whatever the NaI concentration.

Reactions of tris(2-pyridyl)phosphine oxides with electrophiles: Formation of 5-substituted 2, 2′-bipyridyls

The reaction of tris (2-pyridyl)phosphine oxides with benzeneselenenyl chloride in methanol gave the corresponding 5-phenylseleno-2, 2′-bipyridyls together with a small amount of 2, 2′-bipyridyls. Similarly, the reaction with arenesulfenyl chlorides in aqueous acetonitrile afforded two kinds of coupling products, 5-phenylthio-2, 2′-bipyridyls and 2, 2′-bipyridyls. While in the reaction with arenesulfinyl chlorides in aqueous acetonitrile, four corresponding bipyridyl derivatives, 2, 2′-bipyridyls, 5-aryhhio-2, 2′-bipyridyls, 5-arylsulfinyl-2, 2′-bipyridyls, and 5-arylsulfonyl-2, 2′-bipyridyls, were formed.