100366-68-5

Basic information

• Product Name: 6-BROMO-2,2':6',2''-TERPYRIDINE
• Synonyms: 6-BROMO-2,2':6',2''-TERPYRIDINE
• CAS NO: 100366-68-5
• Molecular Formula: C₁₅H₁₀BrN₃
• Molecular Weight: 312.16
• Mol File: 100366-68-5.mol

Chemical Properties

• Boiling Point: 438.5 °C at 760 mmHg
• Flash Point: 219 °C
• Appearance: /
• Density: 1.446 g/cm³
• CAS DataBase Reference: 6-BROMO-2,2':6',2''-TERPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-2,2':6',2''-TERPYRIDINE(100366-68-5)
• EPA Substance Registry System: 6-BROMO-2,2':6',2''-TERPYRIDINE(100366-68-5)

Safety Data

• Hazardous Substances Data: 100366-68-5(Hazardous Substances Data)

Usage

Uses

Used in Coordination Chemistry:
6-BROMO-2,2':6',2''-TERPYRIDINE is used as a ligand for the formation of stable metal complexes, which is crucial in coordination chemistry. Its ability to chelate metal ions contributes to the development of new materials with unique properties and functions.
Used in Materials Science:
In the field of materials science, 6-BROMO-2,2':6',2''-TERPYRIDINE is utilized as a component in the synthesis of advanced materials. Its role in creating metal complexes allows for the engineering of materials with tailored characteristics for specific applications.
Used in Catalysis:
6-BROMO-2,2':6',2''-TERPYRIDINE is employed as a catalyst or a catalyst precursor in various chemical reactions. The metal complexes formed with this compound can accelerate reaction rates and improve the selectivity of certain catalytic processes.
Used in Organic Synthesis:
6-BROMO-2,2':6',2''-TERPYRIDINE is also used in organic synthesis as a building block or intermediate for the creation of more complex organic molecules. Its reactivity and ability to form stable complexes make it a valuable component in the synthesis of pharmaceuticals, dyes, and other organic compounds.
Overall, 6-BROMO-2,2':6',2''-TERPYRIDINE is a significant compound in the realms of chemical research and industrial applications, particularly due to its capacity to form stable complexes with metal ions, which is essential for advancing material development, catalysis, and organic synthesis.

Upstream product

• 1148-79-4 2,2':6,2''-terpyridine 
• 626-05-1 2,6-Dibromopyridine 
• 366-18-7 [2,2]bipyridinyl 
• 149775-39-3 Ethyl 6-(2,2'-pyridyl) sulfoxide 
• 26482-00-8 1-(2-oxo-2-(2-pyridyl)ethyl)pyridinium iodide 
• 100366-65-2 N,N-dimethyl<3-(6'-bromo-2'-pyridyl)-3-oxopropyl>ammonium chloride 
• 100366-67-4 3-Dimethylamino-1-pyridin-2-yl-propan-1-one; hydrochloride 
• 84488-18-6 1-(2-(6-bromopyridin-2-yl)-2-oxoethyl)pyridinium iodide 
• 87905-04-2 (+/-)-2-(ethylsulfinyl)pyridine 
• 10495-73-5 2-bromo-6-(pyridin-2-yl)pyridine 
• 130897-01-7 Ethyl 6-(2,2'-pyridyl) sulfide 
• 109-04-6 2-bromo-pyridine 
• 49669-22-9 6,6'-Dibromo-2,2'-bipyridine 
• 108-36-1 1,3-dibromobenzene 

Downstream Products

• 1185738-82-2 1,3,5-tris(2',2'',6'',2'''-terpyridin-6'-yl)benzene 
• 1332698-87-9 1,3-dibromo-5-(2,2';6',2-terpyridin-6-yl)benzene 
• 1365543-85-6 1,3-bis(2,2'-bipyridin-6-yl)-5-(2,2';6',2-terpyridin-6-yl)benzene 
• 1332698-88-0 1,3-bis(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-(2,2';6',2-terpyridin-6-yl)benzene 
• 1365543-90-3 1,3-bis(2,2';6',2-terpyridin-6-yl)-5-(2,2'-bipyridin-6-yl)benzene 

Relevant articles and documents

Synthesis of ω-(Bromomethyl)bipyridines and Related ω-(Bromomethyl)pyridinoheteroaromatics: Useful Functional Tools for Ligands in Host Molecules

Pyridines and 2,2'-bipyridines have been employed as useful ligands in molecular recognition chemistries.Halomethyl-substituted bipyridine or oligopyridine derivatives were required for the assembly of bipyridine or oligopyridine units with a supporting mother functional part in artificial biofunctional molecules.A series of ω-(bromomethyl)bipyridines and related ω-(bromomethyl)pyridinoheteroaromatic compounds (types I-III) were synthesized in this paper.Preparation of oligopyridines and pyridinoheteroaromatic compounds have been carried out by either intermolecular ligand coupling of alkyl heteroaryl sulfoxide with pyridyllithium or intramolecular ligand coupling of pyridyl heteroaryl sulfoxide with methylmagnesium bromide for the type I compounds.The type II and III compounds were synthesized by addition of pyridyllithium to pyridinecarboxaldehyde.The ω-bromo group was introduced by radical bromination reaction of methylpyridyl group using NBS and BPO (dibenzoyl peroxide) or bromination of ω-(hydroxymethyl)pyridine using a combination of CBr4 and Ph3P.

Self-assembly of transition metal ion complexes of a hybrid pyrazine-terpyridine ligand

A new hybrid pyrazine-terpyridine ligand L (C34H 22N8) and its complexes with different transition metal ions, M (M = Mn(ii) 1, Zn(ii) 2, Fe(ii) 3, Co(ii) 4, Cu(ii) 5 and Cd(ii) 6), have been synthesised. In the presence of a nitrate counter-anion, both Cu(ii) and Cd(ii) give complexes in which the ratio M : L is 2 : 1, whereas with perchlorate, trifluoromethanesulfonate or tetrafluoroborate, the other metal ions provide solids in which this ratio is 1 : 1. From mass spectral measurements and a single crystal, X-ray structure determination for the Fe(ii) complex 3, however, all the latter species are concluded to be 2 : 2 complexes. Both the Fe(ii) complex 3 and the Co(ii) complex 4, generated from tetrafluoroborate reactant salts, have the composition [M2L 2F2(H2O)](BF4)2, the presence of fluoride ligands being presumed to reflect the abstraction of fluoride ions from tetrafluoroborate by the metal ions under the preparative conditions. The crystal structure of complex 3 shows the Fe(ii) centres to be inequivalent, one being high-spin and heptacoordinate with a FeN 4F2O coordination sphere, the other low-spin and octahedral with a FeN6 sphere. The two ligand molecules differ markedly, one being heptadentate, the other clearly hypodentate , with only three N-donor atoms of a terpyridine-like arm coordinated, although their conformations are similar, showing significant differences from that of C2 symmetry found for the free ligand by a crystal structure determination. Mass spectra are consistent with the Cu(ii) and Cd(ii) complexes having the composition [M2L(H2O)n(NO 3)4-n](NO3)4-n, and the weak antiferromagnetic coupling observed for the Cu(ii) complex is consistent with a preliminary crystal structure determination which indicates that the two Cu(ii) centres are not bridged by a pyrazine unit. The Royal Society of Chemistry 2013.

Hypodentate Ligands: Systematic Approaches to Complexes containing Didentate 2,2':6',2''-Terpyridine (terpy) and the Crystal and Molecular Structures of 2 and 2 (bipy=2,2'-bipyridine, bterpy=6-bromo-2,2':6',2''-...)

A series of complexes containing hypodentate didentate 2,2':6',2''-terpyridine (terpy) ligands of general formula 2+ have been prepared.The complexes 2 and 2 (bterpy = 6-bromo-2,2':6',2''-terpyridine) have been structurally characterised and shown to contain the didentate terpy ligand in the solid state.

Metal-Ligand Cooperativity via Exchange Coupling Promotes Iron- Catalyzed Electrochemical CO2Reduction at Low Overpotentials

Biological and heterogeneous catalysts for the electrochemical CO2 reduction reaction (CO2RR) often exhibit a high degree of electronic delocalization that serves to minimize overpotential and maximize selectivity over the hydrogen evolution reaction (HER). Here, we report a molecular iron(II) system that captures this design concept in a homogeneous setting through the use of a redox non-innocent terpyridine-based pentapyridine ligand (tpyPY2Me). As a result of strong metal-ligand exchange coupling between the Fe(II) center and ligand, [Fe(tpyPY2Me)]2+ exhibits redox behavior at potentials 640 mV more positive than the isostructural [Zn(tpyPY2Me)]2+ analog containing the redox-inactive Zn(II) ion. This shift in redox potential is attributed to the requirement for both an open-shell metal ion and a redox non-innocent ligand. The metal-ligand cooperativity in [Fe(tpyPY2Me)]2+ drives the electrochemical reduction of CO2 to CO at low overpotentials with high selectivity for CO2RR (>90%) and turnover frequencies of 100 ?000 s-1 with no degradation over 20 h. The decrease in the thermodynamic barrier engendered by this coupling also enables homogeneous CO2 reduction catalysis in water without compromising selectivity or rates. Synthesis of the two-electron reduction product, [Fe(tpyPY2Me)]0, and characterization by X-ray crystallography, M?ssbauer spectroscopy, X-ray absorption spectroscopy (XAS), variable temperature NMR, and density functional theory (DFT) calculations, support assignment of an open-shell singlet electronic structure that maintains a formal Fe(II) oxidation state with a doubly reduced ligand system. This work provides a starting point for the design of systems that exploit metal-ligand cooperativity for electrocatalysis where the electrochemical potential of redox non-innocent ligands can be tuned through secondary metal-dependent interactions.

METAL-LIGAND CATALYSTS FOR SELECTIVE PROMOTION OF ELECTROCHEMICAL CO2RR

The electrochemical carbon dioxide reduction reaction (CO2RR) provides opportunities to synthesize value-added products from this greenhouse gas in a sustainable manner. Efficient catalysts for this reaction are provided that selectively drive CO2 reduction over the thermodynamic and kinetically competitive hydrogen evolution reaction (HER) in organic or aqueous electrolytes. The catalysts are metal-polypyridyl coordination complexes of a redox non-innocent terpyridine-based pentapyridine ligand and a first-row transition metal. The metal-ligand cooperativity in [Fe(tpyPY2Me)]2+ drives the electrochemical reduction of CO2 to CO at low overpotentials with high selectivity for CO2RR (>90%).

Bi- or ter-pyridine tris-substituted benzenes as electron-transporting materials for organic light-emitting devices

We demonstrated that 1,3,5-tris([2′,2′′]bipyridin- 6′-yl)benzene (BpyB) and 1,3,5-tris([2′,2′′, 6′′,2′′′]terpyridin-6'-yl)benzene (TpyB) are good electron-transport (ET) layer materials for organic light-emitting devices (OLEDs). The new materials exhibit

A convenient high yield synthesis of 2,2′:6′,2″:6″,2?:6?,2″″: 6″″,2″?-sexipyridine and helical transition-metal complexes of substituted sexipyridines

The compound 2,2′:6′,2″:6″,2?:6?,2″″: 6″″,2″?-sexipyridine (spy) has been synthesised in high yield by the coupling of 6-bromo-2,2′:6′,2″-terpyridine with a nickel(0) reagent, followed by demetallation of the resultant double-helical [Ni2(spy)2]4+ complex with KCN. In order to probe the effects of substitution of spy upon helication processes, the substituted compounds 4′,4″″-bis(methylsulfanyl)-2,2′:6′,2″: 6″,2?:6?,2″″:6″″,2″?- sexipyridine (msspy), 4′,4″″-diphenyl-2,2′:6′,2″:6″, 2?:6?,2″″:6″″,2″?- sexipyridine (pspy) and 4′,4″″-bis(4-tert-butylphenyl)-2,2′:6′,2″: 6″,2?:6?,2″″:6″″,2″?- sexipyridine (tbspy) were also prepared and studied. The reaction of each of these compounds with transition-metal ions capable of adopting an octahedral geometry results in the self-assembly of dinuclear double-helical complexes of the type [M2L2]4+ [M = iron(II), cobalt(II), nickel(II), copper(II), zinc(II), cadmium(II) or mercury(II); L = spy, msspy, pspy or tbspy]; the double-helical topology of the zinc complex of pspy was confirmed by a crystal-structure analysis of the salt [Zn2(pspy)2]-[PF6] 4-2MeCN·2H2O [space group P42212, a = 15.518(2), c = 18.443(1) A, R = 0.0638, R′ = 0.0735].

A Templated Synthesis of a Dinickel(II) Double-helicate and its Demetallation to Free 2,2': 6',2'':6'',2''': 6''',2'''': 6'''',2'''''-Sexipyridine

The double-helical complex 4 of the hexadentate ligand 2,2': 6',2'': 6'',2''': 6''',2'''': 6'''',2'''''-sexipyridine (spy) is readilly prepared in good yield in a nickel(0) templated coupling of 6-bromo-2,2': 6',2''-terpyridine.The free ligand is obtained in quantitative yield by demetallation of this complex with cyanide.

Synthesis of Halogenated Terpyridines and Incorporation of the Terpyridine Nucleus into a Polyetheral Macrocycle

Two synthetic approaches to haloterpyridines are herein described.The first method involved direct halogenation of terpyridine N-oxides with POCl3 to generate a mixture of polyhalogenated terpyridines.A more efficient approach to 6,6''-dibromo-2,2':6',2''-terpyridine utilized the Kroehnke synthesis to form the terpyridine moiety from appropriately halosubstituted precursors.Direct nucleophilic substitution on terpyridine was found to give low yields of macrocyclic products; however, if 1,5-bis(6-bromo-2-pyridyl)-1,5-dioxopentane was employed, macrocyclization afforded improved yields of the desired terpyridines.