96517-97-4

Usage

Uses

Used in Organic Synthesis:
2-(Bromomethyl)-6-(6-(bromomethyl)pyridin-2-yl)pyridine is utilized as a key building block in organic synthesis for the creation of various complex organic molecules. Its bromomethyl groups facilitate the formation of new chemical bonds, making it a versatile component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(Bromomethyl)-6-(6-(bromomethyl)pyridin-2-yl)pyridine is employed as an intermediate in the development of new drugs. Its unique structure allows for the attachment of various functional groups, enabling the design of molecules with specific therapeutic properties. 2-(broMoMethyl)-6-(6-(broMoMethyl)pyridin-2-yl)pyridine's reactivity and stability make it suitable for use in the synthesis of drug candidates targeting a range of diseases and conditions.
Used in Agrochemical Industry:
2-(Bromomethyl)-6-(6-(bromomethyl)pyridin-2-yl)pyridine is also used in the agrochemical industry as a precursor for the synthesis of pesticides and other crop protection agents. Its ability to form stable and reactive intermediates contributes to the development of effective and environmentally friendly agrochemicals.
Used in Chemical Research:
In the field of chemical research, 2-(Bromomethyl)-6-(6-(bromomethyl)pyridin-2-yl)pyridine serves as a valuable compound for studying reaction mechanisms and exploring new synthetic pathways. Its unique structure and reactivity provide insights into the behavior of similar compounds and contribute to the advancement of organic chemistry.

Upstream product

• 4411-80-7 6,6'-dimethyl-2,2'-bipyridine 
• 74065-63-7 6,6′-bis(hydroxymethyl)-2,2′-bipyridine 
• 82740-71-4 6-hydroxymethyl-6′-methyl-2,2′-bipyridine 
• 1824-81-3 2-Amino-6-methylpyridine 
• 5315-25-3 2-bromo-6-methylpyridine 
• 96517-98-5 6-(bromomethyl)-6'-methyl-2,2'-bipyridine 
• 937-14-4 3-chloro-benzenecarboperoxoic acid 
• 82740-66-7 6,6'-dimethyl-2,2'-bipyridine 1,1'-di-N-oxide 
• 366-18-7 [2,2]bipyridinyl 
• 7275-43-6 [2,2']bipyridinyl 1,1'-dioxide 
• 4411-83-0 2,2′-bipyridine-6,6′-dicarbonitrile 
• 65739-40-4 6,6′-bis(ethoxycarbonyl)-2,2′-bipyridine 

Downstream Products

• 122768-44-9 6,6'-Bis-[(diphenylphosphanyl)-methyl]-[2,2']bipyridinyl 
• 204320-48-9 (11,14-Dibenzyl-17-benzyloxycarbonylmethyl-10,15-dioxo-8,11,14,17,23,24-hexaaza-tricyclo[17.3.1.1^2,6]tetracosa-1⁽²³⁾,2,4,6⁽²⁴⁾,19,21-hexaen-8-yl)-acetic acid benzyl ester 
• 491571-53-0 2,8-ditosyl-2,5,8-triaza-5-methyl[9]-2,2'-dipyridinophane 
• 447405-32-5 2,8,23,29-tetratosyl-2,5,8,23,26,29-hexaaza-5,26-dimethyl[24]-10,21,31,42-bis-dipyridinophane 
• 868992-07-8 acetic acid 3,5-diacetoxy-2-acetoxymethyl-6-{3-[4-(6'-{4-[3-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propyl]-phenoxymethyl}-[2,2']bipyridinyl-6-ylmethoxy)-phenyl]-propoxy}-tetrahydro-pyran-4-yl ester 
• 122768-51-8 6,6'-Bis-(diphenyl-phosphinoylmethyl)-[2,2']bipyridinyl 

Relevant academic research and scientific papers

Definition of an intramolecular Eu-to-Eu energy transfer within a discrete [Eu2L] complex in solution

Ligand L, based on two do3a moieties linked by the methylene groups of 6,6'-dimethyl-2,2'-bipyridine, was synthesized and characterized. The addition of Ln salts to an aqueous solution of L (0.01 M Tris-HCl, pH 7.4) led to the successive formation of [LnL] and [Ln2L] complexes, as evidenced by UV/Vis and fluorescence titration experiments. Homodinuclear [Ln2L] complexes (Ln=Eu, Gd, Tb, Yb, and Lu) were prepared and characterized. The 1H and 13C NMR spectra of the Lu and Yb complexes in D2O solution (pD=7.0) showed C1 symmetry of these species in solution, pointing to two different chemical environments for the two lanthanide cations. The analysis of the chemical shifts of the Yb complex indicated that the two coordination sites present square antiprismatic (SAP) coordination environments around the metal ions. The spectroscopic properties of the [Tb2L] complex upon ligand excitation revealed conventional behavior with τH2O=2.05(1) ms and φH2O=51 %, except for the calculation of the hydration number obtained from the luminescent lifetimes in H2O and D2O, which pointed to a non-integer value of 0.6 water molecules per TbIII ion. In contrast, the Eu complex revealed surprising features such as: 1) the presence of two and up to five components in the 5D0→7F0 and 5D0→7F1 emission bands, respectively; 2) marked differences between the normalized spectra obtained in H2O and D2O solutions; and 3) unconventional temporal evolution of the luminescence intensity at certain wavelengths, the intensity profile first displaying a rising step before the occurrence of the expected decay. Additional spectroscopic experiments performed on [Gd 2-xEuxL] complexes (x=0.1 and 1.9) confirmed the presence of two distinct Eu sites with hydration numbers of 0 (site I) and 2 (site II), and showed that the unconventional temporal evolution of the emission intensity is the result of an unprecedented intramolecular Eu-to-Eu energy-transfer process. A mathematical model was developed to interpret the experimental data, leading to energy-transfer rates of 0.98 ms-1 for the transfer from the site with q=0 to that with q=2 and vice versa. Hartree-Fock (HF) and density functional theory (DFT) calculations performed at the B3LYP level were used to investigate the conformation of the complex in solution, and to estimate the intermetallic distance, which provided Foerster radii (R0) values of 8.1 A for the energy transfer from site I to site II, and 6.8 A for the reverse energy transfer. These results represent the first evidence of an intramolecular energy-transfer equilibrium between two identical lanthanide cations within a discrete molecular complex in solution. Copyright

Determination of the absolute configuration and identity of chiral carboxylic acids using a Cu(II) complex of pyridine-benzimidazole-based ligand

We report a new achiral Cu host [Cu(bmb-bpy)(H2O)(OTf) 2] (bmb-bpy = 6,6′-bis[((1-methylbenzimidazol-2-yl)thio)methyl] -2,2′-bipyridine) for the enantioselective and chemoselective recognition of chiral carboxylic acids. The binding of chiral carboxylic acids to [Cu(bmb-bpy)(H2O)(OTf)2] produced an exciton-coupled circular dichroism signal; the linear discriminant analysis allowed the assignment of the absolute configuration, enantiomeric excess, and identity of chiral carboxylic acids.

Novel ruthenium complexes bearing bipyridine-based and N-heterocyclic carbene-supported pyridine (NCN) ligands: The influence of ligands on catalytic transfer hydrogenation of ketones

Transfer hydrogenation (TH) is a powerful synthetic tool in the production of secondary alcohols from ketones by using a non-H2hydrogen source along with metal catalysts. Among homogeneous catalysts, Ru(ii) complexes are the most efficient catalysts. In our research, six novel ruthenium(ii) complexes bearing bipyridine-based ligands [Ru(L1)Cl2] (1), [Ru(L1)(PPh3)Cl]Cl (2) and [Ru(L2)Cl2] (3) and N-heterocyclic carbene-supported pyridine (NCN) ligands [RuCp(L3)]PF6(4), [RuCp*(L3)]PF6(5), and [Ru(p-cymene)(L3)Cl]PF6(6) (whereL1= 6,6′-bis(aminomethyl)-2,2′-bipyridine,L2= 6,6′-bis(dimethylaminomethyl)-2,2′-bipyridine andL3= 1,3-bis(2-methylpyridyl)imidazolium bromide) were synthesised and characterised by NMR spectroscopy, HRMS, and X-ray crystallography. The catalytic transfer hydrogenation of 28 ketones in 2-propanol at 80 °C in the presence of KOtBu (5 mol%) was demonstrated and the effect of ligands is highlighted. The results show that catalyst1exhibits improved TH efficiency compared to the commercially available Milstein catalyst and displays higher catalytic activity than2due to the steric effect from PPh3. From a combination of kinetic data and Eyring analysis, a zero-order dependence on the acetophenone substrate is observed, implying a rate-limiting hydride transfer step, leading to the proposed inner-sphere hydride transfer mechanism.

Thermally induced transformation of a Cu4I4-based cluster to a Cu2I2-based cluster under mild conditions

A reaction of 6,6′-bis((benzylthio)methyl)-2,2′-bipyridine (L) with CuI at room temperature led to one Cu4I4-based cluster, which could be thermally transformed to a Cu2I2-based one under mild conditions due to the formation of a Cu-S bond. Along with the structural transformation, remarkable changes in the color and luminescence have been triggered.

Dynamic Helicates Self-Assembly from Homo- and Heterotopic Dynamic Covalent Ligand Strands

The understanding and the application of reversible covalent reactions and coordination chemistry together with the proper design of the molecular frameworks, allow to achieve not only well-defined output architectures but also different grades of complex behavior. In this work, the dynamic nature of the helical systems offers an additional level of complexity by combining self-sorting on two levels: 1) the build-up of the ligand strand constituents from their components through dynamic covalent chemistry; 2) the assembly of the helicates from the ligands and the metal cations through dynamic metallo-supramolecular chemistry. The information encoded in the ligands constituent molecule was read differently (and accurately at the same time) by metal cations that varied in the coordination algorithms. It enabled the selective formation of a specific type of helicates from a wide library of helicates formed by the possible combination of subcomponents. Ligands containing dynamic tridentate and/or bidentate binding motifs in the same strand were studied to explore the helicates self-assembly with appropriate metal cations.

Upconverted photosensitization of Tb visible emission by NIR Yb excitation in discrete supramolecular heteropolynuclear complexes

Addition of Tb3+ salts to a solution of a (YbLD) complex in D2O resulted in the formation of [(YbLD)2Tbx] (x = 1 to 3) complexes that, upon NIR excitation at 980 nm, showed an unprecedented Yb to Tb upconversion sensitization phenomenon resulting in the observation of the typical green emission of Tb.

Improved Halogenation of Methyl Aromatics and Methyl Heteroaromatics: Unexpected Reactivity of Tetrahalogeno-diphenylglycolurils

1,3,4,6-Tetrachloro (TCDGU) and 1,3,4,6-tetrabromo-3α,6α-diphenylglycolurils smooth halogen oxidizers have been exploited in a new direction as reagents for free radical substitution toward some N-halosuccinimide nonreactive bis-heterocycles. An unexpected selectivity and reactivity were observed with methyl benzenes, methyl heterocycles, and methyl-bis-heterocycles of interest. A chemometric study has been performed to optimize five independent factors of the chlorination reaction with TCDGU. The predictive model was established either for the halogenation conversion and the ratio of monochlorination.

Design and synthesis of new Ru-complexes as potential photo-sensitizers: Experimental and TD-DFT insights

We report density functional theory (DFT) and time-dependent density functional theory (TDDFT) calculations on a novel organic ligand and a novel class of ruthenium complexes; cis-RuL2X2 with L = 2,2′-bipyridine-6,6′-bis ethyl ester phosphonate and phosphonic acid, X = Cl, CN or NCS. The calculations show that cis-configurations are more stable than the trans-counterparts. The DFT results have been used to help design such novel complexes for potential use as sensitizers. We demonstrate the opportunity to synthesize such complexes with high purity. The synthesis of these complexes relies on the preparation of the key intermediates cis-Ru(2,2′-bipyridine-6,6′-bisdiethyl ester phosphonate)Cl2. These complexes were characterized by 1H, 13C, and 31P NMR, elemental analysis and FTIR spectroscopy. The NCS complex shows the smallest optical band gap followed by the Cl and CN complexes, respectively, with the highest performance upon use as a sensitizer in dye-sensitized solar cells.

Step by Step Assembly of Polynuclear Lanthanide Complexes with a Phosphonated Bipyridine Ligand

The synthesis of the octadentate ligand L (LH8 = ((([2,2′-bipyridine]-6,6′-diylbis(methylene))bis(azanetriyl))tetrakis(methylene))tetrakis(phosphonic acid)) is reported. The coordination of L with various lanthanide cations was monitored by absorption and luminescence spectrophotometric titration experiments (Ln = Tb, Yb), potentiometry (Ln = La, Eu, Lu), and mass spectrometry (Ln = Tb). It was found that L forms very stable mononuclear (LnL) species in aqueous solutions (log K = 19.80(5), 19.5(2), and 19.56(5) for La, Eu, and Lu, respectively) with no particular trend along the series. Spectroscopic data showed the Ln cations to be enclosed in the cavity formed by the octadentate ligand, thereby shielding the metal from interactions with water molecules in the first coordination sphere. When more than one equivalent of cations is added, the formation of polynuclear [(LnL)2Lnx] complexes (x = 1-3) can be observed, the presence of which could be confirmed by electrospray and MALDI mass spectrometry experiments. DFT modeling of the mononuclear (LnL) complexes indicated that the coordination of the cation in the cavity of the ligand results in a very asymmetric charge distribution, with a region of small negative electrostatic potential on the hemisphere composed of the chromophoric bipyridyl moiety and an electron-rich domain at the opposite hemisphere around the four phosphonate functions. DFT further showed that this polarization is most likely at the origin of the strong interactions between the (LnL) complexes and the incoming additional cations, leading to the formation of the polynuclear species. 1H and 31P NMR were used to probe the possible exchange of the lanthanide complexed in the cavity of the ligand in D2O, revealing no detectable exchange after 4 weeks at 80 °C and neutral pD, therefore pointing out an excellent kinetic inertness.

Template synthesis and spectral characterization of new Lead(II)-Schiff base macrocyclic complexes incorporating phenanthroline and/or bipyridine units

Lead(II) complexes of Schiff-bases containing phenanthroline and/or bipyridine units were synthesized by the template reaction between new diamine compound, 6,6'-bis(2-aminophenoxymethyl)-2,2'-bipyridine and 2,2-bipyridine-6,6-dicarboxaldehyde or 1,10-phenanthroline- 2,9-dicarboxaldehyde in the presence of metal ions. These complexes, [PbL1]( ClO4)2and [PbL2](NO3)2, were characterized and investigated by using; MALDI-TOF and Q-TOF-MS spectroscopy, FTIR, UV/Visible spectroscopy, 1H NMR, Elemental analyses (CHN), magnetic susceptibility and molar conductivity measurements.