28020-73-7

Basic information

• Product Name: 2,6-BIS(2-BENZIMIDAZOLYL)PYRIDINE
• Synonyms: 2,6-Di(1H-benzo[d]imidazol-2-yl)pyridine;1H-BenziMidazole,2,2'-(2,6-pyridinediyl)bis-;2,6-Bis(1H-benzo[d]iMidazol-2-yl)pyridine;2,2'-(2,6-Pyridinediyl)bis(benzimidazole);2,6-Bis(2-benziMidazolyl)pyridine 98%;2,6-Bis(1H-benzimidazol-2-yl)pyridine;2,6-Bis(benzimidazol-2'-yl)pyridine;2,6-Bis(benzimidazol-2-yl)pyridine
• CAS NO: 28020-73-7
• Molecular Formula: C₁₉H₁₃N₅
• Molecular Weight: 311.34
• EINECS: 1312995-182-4
• Product Categories: C9 to C46;Heterocyclic Building Blocks;Pyridines
• Mol File: 28020-73-7.mol
• Article Data: 43

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 664 °C at 760 mmHg
• Flash Point: 311.4 °C
• Appearance: /
• Density: 1.386 g/cm³
• Vapor Pressure: 1.68E-17mmHg at 25°C
• Refractive Index: 1.78
• Storage Temp.: 2-8°C
• PKA: 10.36±0.10(Predicted)
• CAS DataBase Reference: 2,6-BIS(2-BENZIMIDAZOLYL)PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-BIS(2-BENZIMIDAZOLYL)PYRIDINE(28020-73-7)
• EPA Substance Registry System: 2,6-BIS(2-BENZIMIDAZOLYL)PYRIDINE(28020-73-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 28020-73-7(Hazardous Substances Data)

Usage

Description

2,6-Bis(2-benzimidazolyl)pyridine is a V-shaped ligand that acts as a tridentate nitrogen donor, capable of forming complexes with various compounds. It is known for its ability to serve as an efficient anion receptor, providing chemical shift and optical modification based signals for the detection of specific ions and molecules.

Uses

Used in Chemical Sensing Applications:
2,6-Bis(2-benzimidazolyl)pyridine is used as a chemosensor for the detection of fluoride ions, which are essential for various biological processes but can be harmful in high concentrations. Its ability to detect toxic metabolites of benzene, such as phenol, hydroquinone, resorcinol, catechol, and p-benzoquinone, makes it a valuable tool in environmental monitoring and industrial safety.
Used in Anion Recognition:
As an efficient anion receptor, 2,6-bis(2-benzimidazolyl)pyridine is employed for the detection of acetate ions. This application is crucial in various fields, including water quality assessment, pharmaceutical analysis, and chemical research.
Used in Optical Sensing:
2,6-Bis(2-benzimidazolyl)pyridine is also reported as an optical sensor useful for the recognition of aniline, an important chemical intermediate in the synthesis of various polymers, dyes, and pharmaceuticals. Its ability to detect aniline can be beneficial in monitoring industrial processes and ensuring product quality.
Used in Complex Formation:
The ligand reacts with UO2Cl2·3THF to form complexes, which can be useful in various chemical and materials science applications, such as nuclear fuel reprocessing, catalysis, and the development of new materials with unique properties.

InChI:InChI=1/C19H13N5/c1-2-7-13-12(6-1)21-18(22-13)16-10-5-11-17(20-16)19-23-14-8-3-4-9-15(14)24-19/h1-11H,(H,21,22)(H,23,24)

Synthetic route

Pyridine-2,6-dicarboxylic acid (499-83-2) + 1,2-diamino-benzene (95-54-5) → 2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7)

Conditions	Yield
With phosphoric acid at 220℃; for 4h;	96%
With polyphosphoric acid at 200℃; for 6h;	95%
With phosphoric acid at 220℃; for 5h;	92%

2,6-bis{[(2-aminophenyl)imino]methyl}pyridine → 2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7)

Conditions	Yield
With iodine In methanol; dichloromethane for 5h;	94%

Cu(OAc)2*2,6-bis(benzoimidazolyl)pyridine → 2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7)

Conditions	Yield
With sodium sulfide In methanol for 0.5h;	85%

[Cu(2,6-bis(1H-benzo[d]imidazol-2-yl)pyridine)(H2O)2](SO3CF3)2 → 2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7)

Conditions	Yield
With L-Cysteine In aq. buffer at 25℃; for 1h; pH=7.34; Concentration; Time; Inert atmosphere;

2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7) + UO2Cl2(THF)3 → [UO2(H2BBP)Cl2]

Conditions	Yield
With pyridine for 1h; Inert atmosphere;	98%

2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7) → 2,6-bis(5-nitro-1H-benzo[d]imidazol-2-yl)pyridine (866604-68-4)

Conditions	Yield
With sulfuric acid; nitric acid for 4h; Cooling with ice;	97%

ferrous(II) sulfate heptahydrate + 2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7) + ammonium hexafluorosilicate → iron (II) hexafluorosilicate

Conditions	Yield
With ascorbic acid In ethanol	96%

2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7) + diethyl (4-bromobutyl)phosphonate (63075-66-1) → 2,6-bis(1-(4-diethylphosphonyl)butylbenzimidazol-2-yl)pyridine

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 10h;	95%

2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7) + AuCl4H4(1-)*K(1+) → C19H11AuClN5(1+)

Conditions	Yield
With sodium acetate In methanol for 2h; Reflux;	95%

2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7) + potassium tetrachloroaurate(III) + water (7732-18-5) → C19H11AuClN5*H2O (1431846-31-9)

Conditions	Yield
With sodium acetate In methanol for 2h; Reflux;	95%

ferrous(II) sulfate heptahydrate + 2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7) + B10H10(2-)*2K(1+)*2H2O → [Fe(II)(2,6-bis(benzimidazol-2-yl)pyridine)2]*[B10H10]*2H2O

Conditions	Yield
With ascorbic acid In ethanol; water for 5h; Heating;	95%

2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7) + potassium tetrachloroaurate(III) → C19H11AuClN5

Conditions	Yield
Stage #1: 2,6-bis(benzimidazole-2'-yl)pyridine With sodium acetate In methanol at 50℃; for 0.5h; Stage #2: potassium tetrachloroaurate(III) In methanol at 50℃; for 12h;	94%

2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7) + zinc(II) nitrate hexahydrate + water (7732-18-5) + saccharin sodium salt (128-44-9) → [zinc(II)(2,6-bis(2-benzimidazolyl)pyridine)2](saccharinate)2 dihydrate

Conditions	Yield
In methanol at 60℃; for 4h;	94%

2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7) + iron(II) bromide → 2,6-bis(2-benzimidazolyl)pyridine iron dibromide (1184194-98-6)

Conditions	Yield
In tetrahydrofuran (Ar); std. Schlenk technique; mixt. of ligand and FeBr2 in THF was stirred at room temp. for 1 h and at 60°C for 4 h; cooled to room temp.; filtered; washed (Et2O); dried (vac.); elem. anal.;	93%

oxovanadium(IV) sulfate + 2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7) → VO(2,6-bis(benzimidazolyl)pyridine)(H2O)(SO4)

Conditions	Yield
In ethanol Reflux;	93%

2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7) + water (7732-18-5) + saccharin sodium salt (128-44-9) + copper dichloride → [Cu(saccharinate)2(2,6-bis(2-benzimidazolyl)pyridine)]*3DMF

Conditions	Yield
In methanol at 55℃; for 4h;	93%

2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7) + chromium(III) chloride (10025-73-7) → [2,6-bis(2-benzimidazolyl)pyridyl]chromium(III) chloride (307990-84-7)

Conditions	Yield
With Zn-Hg amalgam In ethanol CrCl3 placed in filter thimble of Soxhlet extractor with Zn-Hg amalgam and soln. of ligand added to reservoir flask, N2 bubbled for 10 min before heating, then CrCl3 extd.; filtered with vac., elem. anal.;	92.6%

2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7) + manganese (II) nitrate tetrahydrate + water (7732-18-5) + saccharin sodium salt (128-44-9) → [Mn(NO3)(saccharinate)(H2O)(2,6-bis(2-benzimidazolyl)pyridine)]*2DMF

Conditions	Yield
In methanol at 55℃; for 4h;	92%

2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7) + water (7732-18-5) + copper(II) bis(trifluoromethanesulfonate) (34946-82-2) → [Cu(2,6-bis(1H-benzo[d]imidazol-2-yl)pyridine)(H2O)2](SO3CF3)2

Conditions	Yield
In methanol at 55℃; for 0.5h; Inert atmosphere;	91.4%

2,6-bis(benzimidazole-2'-yl)pyridine (28020-73-7) + cadmium chloride tetrahydrate → Cd(C5NH3(C7N2H5)2)Cl2*H2O

Conditions	Yield
In methanol a methanol soln. of the ligand was added to a methanol soln. of the Cd salt at room temp.; filtered, washed with methanol, acetone, ether, dried in a vac. desiccator over P4O10; elem. anal.;	91%

Upstream product

• 499-83-2 Pyridine-2,6-dicarboxylic acid 
• 95-54-5 1,2-diamino-benzene 

Downstream Products

• 955363-72-1 2,6-bis(1'-benzylbenzimidazol-2'-yl)pyridine 
• 668984-11-0 [Cr(2,6-bis(benzimidazol-2-yl)pyridine^(1-))2]Cl 
• 112362-30-8 2,6-bis(1-methyl-1H-benzo[d]imidazol-2-yl)pyridine 
• 1315594-62-7 NC₅H₃(CNC₆H₄NCH₂C₆H₂(CH₃)3)2 
• 939397-74-7 [Ru(2,6-bis(2-benzimidazolyl)pyridine)(PPh₃)₂Cl][Cl] 
• 1315594-63-8 NC₅H₃(CNC₆H₄NCH₂C₆H(CH₃)4)2 

Relevant articles and documents

Synthesis and crystal structure of a 3-D netlike supramolecular cobalt picrate complex with 2, 6-bis(benzimidazol-2-yl)pyridine

A novel complex of cobalt picrate with 2, 6-bis(benzimidazol-2-yl)pyridine (L), has been prepared and characterized by elemental analysis, IR spectroscopy, and single-crystal X-ray diffraction. The complex crystallizes in the monoclinic system, space group c2/c with a = 21.8756(6) A, b = 12.2995(3) A, c = 27.4827(7) A, β = 95.6060(10)°, and Z = 4. The structure was refined to the final R1 = 0.0708. The complex units are linked by π-π interactions and hydrogen bonds to give infinite two-dimensional (2-D) supramolecular layers, which are further linked by the intermolecular hydrogen bonds to form a three-dimensional (3-D) netlike supramolecule. Copyright Taylor & Francis Group, LLC.

Probing the Effects of Ligand Field and Coordination Geometry on Magnetic Anisotropy of Pentacoordinate Cobalt(II) Single-Ion Magnets

In this work, the effects of ligand field strength as well as the metal coordination geometry on magnetic anisotropy of pentacoordinated CoII complexes have been investigated using a combined experimental and theoretical approach. For that, a strategic design and synthesis of three pentacoordinate CoII complexes [Co(bbp)Cl2]·(MeOH) (1), [Co(bbp)Br2]·(MeOH) (2), and [Co(bbp)(NCS)2] (3) has been achieved by using the tridentate coordination environment of the ligand in conjunction with the accommodating terminal ligands (i.e., chloride, bromide, and thiocyanate). Detailed magnetic studies disclose the occurrence of slow magnetic relaxation behavior of CoII centers with an easy-plane magnetic anisotropy. A quantitative estimation of ZFS parameters has been successfully performed by density functional theory (DFT) calculations. Both the sign and magnitude of ZFS parameters are prophesied well by this DFT method. The theoretical results also reveal that the α → β (SOMO-SOMO) excitation contributes almost entirely to the total ZFS values for all complexes. It is worth noting that the excitation pertaining to the most positive contribution to the ZFS parameter is the dxy → dx2-y2 excitation for complexes 1 and 2, whereas for complex 3 it is the dz2 → dx2-y2 excitation.

Rational design of ruthenium complexes containing 2,6-bis(benzimidazolyl)pyridine derivatives with radiosensitization activity by enhancing p53 activation

Abstract The rational design of metal-based complexes is an effective strategy for the discovery of potent sensitizers for use in cancer radiotherapy. In this study, we synthesized three ruthenium complexes containing bis-benzimidazole derivatives: Ru(bbp)Cl3 (1), [Ru(bbp)2]Cl2 (2 a) (in which bbp=2,6-bis(benzimidazol-1-yl)pyridine), and [Ru(bnbp)2]Cl2 (2 b) (where bnbp=2,6-bis-(6-nitrobenzimidazol-2-yl)pyridine). We evaluated their radiosensitization capacities in vitro and mechanisms of action. Complex 2 b was found to be particularly effective in sensitizing human melanoma A375 cells toward radiation, with a sensitivity enhancement ratio of 2.4. Along with this potency, complex 2 b exhibited a high degree of selectivity between human cancer and normal cells. Mechanistic studies revealed that 2 b promotes radiation-induced accumulation of intracellular reactive oxygen species (ROS) by reacting with cellular glutathione (GSH) and then causing DNA stand breaks. The subsequent DNA damage induces phosphorylation of p53 (p-p53) and upregulates the expression levels of p21, which inhibits the expression of cyclin-B, leading to G2M arrest. Moreover, p-p53 activates caspases-3 and -8, triggers cleavage of poly(ADP-ribose) polymerase (PARP), finally resulting in apoptosis. Taken together, the results of this study provide a strategy for the design of ruthenium-based radiosensitizers for use in cancer therapy.

Toward equatorial planarity about uranyl: Synthesis and structure of tridentate nitrogen-donor {UO2}2+ complexes

The reaction of UO2Cl2·3THF with the tridentate nitrogen donor ligand 2,6-bis(2-benzimidazolyl)pyridine (H 2BBP) in pyridine leads to the formation of three different complexes: [(UO2)(H2BBP)Cl2] (1), [(UO) 2(HBBP)(Py)Cl] (2), and [(UO2)(BBP)(Py)2] (3) after successive deprotonation of H2BBP with a strong base. Crystallographic determination of 1-3 reveals that increased charge through ligand deprotonation and displacement of chloride leads to equatorial planarity about uranyl as well as a more compact overall coordination geometry. Near-Edge X-ray Absorption Fine Structure (NEXAFS) spectra of 1-3 at the U-4d edges have been recorded using a soft X-ray Scanning Transmission X-ray Microscope (STXM) and reveal the uranium 4d5/2 and 4d3/2 transitions at energies associated with uranium in the hexavalent oxidation state. First-principles Density Functional Theory (DFT) electronic structure calculations for the complexes have been performed to determine and validate the coordination characteristics, which correspond well to the experimental results.

Synthesis, structure, and supramolecular chemistry of three azide manganese complexes with 2, 6-Bis(benzimidazol-2-yl)pyridine

Three azide complexes with the tridentate ligand 2, 6-bis(benzimidazol-2- yl)pyridine (H2BBIP) were synthesized and their complicated supramolecular interactions were investigated with single-crystal X-ray diffraction. Interestingly, the complexes are assembled by bifurcated hydrogen bonding, double helical π-π stacking, or anion-π stacking interactions of the benzimidazole rings by tuning the reaction conditions (temperature, ratio, solvent). Complex 1 is a mononuclear compound, namely, Mn(H 2BBIP)N3(CH3O)·CH3OH. In its 3D supramolecular network, the nitrogen atom of the azide anion is acting as hydrogen bonding bifurcated acceptor. Complex 2 is a dinuclear compound, namely, Mn2(H2BBIP)2(N3) 2·(H2O)0.5. The dinuclear unit is connected by intramolecular π-π stacking interactions. Furthermore, double helical π-π stacking interactions in the benzimidazole rings are observed. Complex 3, Mn2(H2BBIP)2(N 3)2·CH3OH, can be formulated as a pseudopolymorph of complex 2, which exhibits intramolecular π-π stacking interactions as well as anion-π interactions in the dinuclear unit. Copyright

Pure white OLED based on an organic small molecule: 2,6-Di(1H-benzo[d]imidazol-2-yl)pyridine

Abstract 2,6-Di(1H-benzo[d]imidazol-2-yl)pyridine (DBIP) was synthesized. The single-crystal structure of DBIP was resolved. DBIP-based OLED was fabricated. The electroluminescence for the device corresponds to a pure white emission. In addition, thermal stability, UV-vis, photoluminescence and electrochemical behaviors of DBIP were investigated as well.

Synthesis, characterization, DNA binding and cleavage studies of mixed-ligand Cu(II) complexes of 2,6-bis(benzimidazol-2-yl)pyridine

Four novel copper(II) complexes of the composition [CuLX] where L = 2,6-bis(benzimidazole-2yl)pyridine, X = dipyridophenazine (L1), 1,10-phenanthroline (L2), hydroxyproline (L3) and 2,6-pyridine dicarboxylic acid (L4) were synthesized and characterized by using elemental analysis, FT-IR, UV-vis, ESI-MS, molar conductance and magnetic susceptibility measurements. The complexes [CuLL 1] (NO3)2 [1], [CuLL2](NO 3)2 [2], [CuLL3](NO3) [3] and [CuLL4] (NO4) [4] are stable at room temperature. In DMSO the complexes [1] and [2] are 1:2 electrolytes, [3] and [4] are 1:1 electrolytes. Based on elemental and spectral studies five coordinated geometry is assigned to all the four complexes. The interaction of four copper ion complexes with calf thymus DNA were carried out by UV-vis titrations, fluorescence spectroscopy, thermal melting and viscosity measurements .The binding constant (Kb) of the above four metal complexes were determined as 5.43× 104 M, -1 2.56×10 4 M-1, 1.21×104 M-1 and 1.57× 104 M-1 respectively. Quenching studies of the four complexes indicates that these complexes strongly bind to DNA, out of all complex 1 is binding more strongly. Viscosity measurements indicate the binding mode of complexes with CT DNA by intercalation through groove. Thermal melting studies also support intercalative binding. The nuclease activity of the above metal complexes shows that 1, 2 and 3 complexes cleave DNA through redox chemistry. Springer Science+Business Media, LLC 2012.

Synthesis, characterization, and antimicrobial properties of two cu(II) complexes derived from a benzimidazole ligand

Two copper(II) complexes, [Cu(L)2](ClO4)2] and [Cu(L)(bipy)](ClO4)2, were prepared and characterized by the spectroscopic and analytic methods, where L is N-butylbenzimidazole and bipy is 2,2’-bipyridine. Single crystals of [Cu(L)(bipy)](ClO4)2 suitable for X-ray diffraction study were obtained by slow diffusion of diethyl ether into a DMF solution of the complex and the complex was found to crystallize as [Cu(L)(bipy)](ClO4)2·DMF. The asymmetric unit contains one [Cu(L) (bipy)]2+, two uncoordinated perchlorates, and one DMF solvate. Coordination geometry around Cu (II) is distorted square pyramidal with τ value of 0.31. Thermal properties of the complexes were examined by thermogravimetric analysis, indicating that the complexes are thermally stable to 310°C. The metal complexes were screened for their in vitro antibacterial and antifungal activities Bacillus subtilis and Bacillus cereus (as Gram(+) bacteria), Escherichia coli, Enterobacter aerogenes, and Klebsiella pneumoniae (as Gram(–) bacteria), and Saccharomyces cerevisiae, Candida utilis, and Candida albicans (as yeasts). The complexes show antibacterial and antifungal activities against bacteria and yeasts.

Bis(benzimidazole)pyridine derivative as a new class of G-quadruplex inducing and stabilizing ligand

Two new bis(benzimidazole)aryl derivatives have been prepared and one of them has been shown to induce and stabilize formation of a G-quadruplex. The Royal Society of Chemistry.

Synthesis, crystal structure, and DNA-binding of a 3-D netlike supramolecular manganese picrate complex with 2,6-bis(benzimidazol-2-yl)pyridine

Manganese picrate with 2,6-bis(benzimidazol-2-yl)pyridine (L) has been prepared and characterized by elemental analysis, IR spectroscopy, and single-crystal X-ray diffraction. The complex crystallizes in the triclinic system, space group P-1 with a=14.234(3) A, b=14.324(2)A, c=15.242(2)A, α=77.569(2)°, β=63.350(3)°, γ=82.130(2)°, and Z= 2. Interaction of the complex with calf-thymus DNA (CT-DNA) has been investigated with diverse spectroscopic techniques and viscosity measurements, and the binding constant is 1.76×10-5mol-1. Results suggest that the complex bind to CT-DNA via intercalation.

A New Protocol for Catalytic Reduction of Alkyl Chlorides Using an Iridium/Bis(benzimidazol-2′-yl)pyridine Catalyst and Triethylsilane

The reduction of alkyl chlorides using triethylsilane is investigated. Primary, secondary, tertiary, and benzylic C-Cl bonds are effectively converted into C-H bonds using an [IrCl(cod)] 2/2,6-bis(benzimidazol-2′-yl)pyridine catalyst system. This catalyst system is quite simple since the tridentate N-ligand can be easily prepared in one step from commercially available reagents.

Platinum (II) complex/sodium deoxycholate hybrid material and preparation and application thereof

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Selective and high yield transformation of glycerol to lactic acid using NNN pincer ruthenium catalysts

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