69506-92-9

Usage

Family

Polyamine compounds

Structure

Benzene ring with two imidazole groups attached at the 1 and 3 positions, each connected by a methyl bridge

Applications

a. Organic synthesis
b. Coordination chemistry
c. Ligand in metal-organic frameworks

Uses

Building block for the synthesis of various organic molecules

Biological activities

Investigated for potential as an anti-cancer agent

Versatility

Potential uses in a variety of fields due to unique structural and chemical properties

Upstream product

• 288-32-4 1H-imidazole 
• 626-15-3 1,3-bis-(bromomethyl)benzene 
• 20671-53-8 potassium 1H-imidazolide 
• 620-13-3 1-bromomethyl-3-methyl-benzene 
• 108-38-3 m-xylene 
• 1477-55-0 1,3-di(aminomethyl)benzene 
• 616-02-4 citraconic acid anhydride 
• 623-25-6 p-Xylylene dichloride 
• 626-16-4 3-(chloromethyl)benzyl chloride 

Relevant academic research and scientific papers

Synthesis and Characterization of a Cu2(pzdc)2(bix) [pzdc: 2,3-pyrazinedicarboxylate; Bix: 1,3-bis(imidazol-1-yl)benzene] Porous Coordination Pillared-Layer Network

A porous coordination polymer (PCP) was prepared using pyrazine-2,3-dicarboxylate (pzdc) and the pillar ligand 1,3-bis(imidazol-1-yl)benzene) (bix) in an attempt to improve on the thermal stability and adsorption properties of Cu2(pzdc)2(L) (L = pillar ligand; typically dipyridyl-based). As-synthesized Cu2(pzdc)2(bix) showcases a highly crystalline structure (Monoclinic, P21/c, a = 11.836 ?, b = 13.005 ?, c = 11.389 ?, β = 107.64°) that exhibits characteristic diffraction peaks also found in the dipyridyl-based PCP counterparts. Thermal analysis based on results from thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC) and in situ high temperature X-ray diffraction (XRD) suggests both framework contraction and expansion during the elimination of physisorbed and coordinated water, phase transition, and prior to the eventual destruction of the structure, which takes place at ca. 556 K. The thermal stability limit is an improvement over those displayed by other Cu2(pzdc)2(L) materials by an average margin of ca. 55 K. Comparison of the adsorption of CO2 vs N2 both at cryogenic temperatures suggests a concomitant structural expansion in the presence of the former. This process appears to take place even at ambient temperatures and CO2 pressures up to 50 atm; the isotherm profile showcases a hysteretic pathway and full adsorption saturation is not apparent. Furthermore, evaluation of CO2 adsorption at different equilibration time intervals indicate that the structure relaxation time scale is larger than that of the adsorption kinetics; similar observations have been made before for Cu2(pzdc)2(bpy) (bpy: 4,4′-bipyridine). The presence of the imidazole groups, however, results in greater interactions with CO2 (maximum ΔHiso ～ 32 kJ mol-1). Selectivity for CO2 over CH4 (10/90) based on the Ideal Adsorbed Solution Theory (IAST) reaches 8.4, which is a 10% and 75% increase when compared against Cu2(pzdc)2(bpy) and Cu2(pzdc)2(bpe) (bpe: 1,2-di(4-pyridyl)-ethylene).

Influence of ligand composition on crystal structure formation-isostructurality and morphotropism

Two new Ag(i) complexes with 1,3-bis(imidazol-1-ylmethyl)benzene (L1) and 1,3-bis(imidazol-1-ylmethyl)-5-methylbenzene (L2), namely {[AgL1]CF3SO3}n (1) and {[AgL2]CF3SO3}n (2), were synthesised and characterised by SCXRD to uncover the effect that introdu

Assembly of a series of coordination polymers built from rigid a tetracarboxylate ligand and flexible bis(imidazole) linker: Syntheses, structural diversities, luminescence sensing, and photocatalytic properties

Hydrothermal reactions of aromatic terphenyl-4,2′′,5′′,4′-tetracarboxylic acid (H4tta) and transitional metal cations in the presence of two flexible N-donor ancillary ligands afforded four novel coordination polymers, namely, {[Zn(tta)0.5(m-bimb)]·H2O}n (1), [Ni2(tta)(m-bimb)2(H2O)]n (2), [Ni(H2tta)(o-bimb)·H2O]n (3), and [Cd(tta)0.5(o-bimb)]n (4), from solvothermal reactions in the presence of bis(imidazole) bridging linkers (m-bimb = 1,3-bis(imidazol-1-ylmethyl)benzene, and o-bimb = 1,2-bis(imidazol-1-ylmethyl)benzene). Their structures were determined by single-crystal X-ray diffraction analyses and further characterized by elemental analyses (EA), powder X-ray diffraction (PXRD), and thermogravimetric (TG) analyses. Compound 1 displayed a 2-fold 3D → 3D parallel entangled (4,4)-connected bbf net with the point symbol of (64·82)(66)2. Compound 2 featured a predocumented 3D (4,8)-connected (32·53·6)(34·44·59·611) net. Compound 3 exhibited a 2D 4-connected SQL sheet with the point symbol of (44·62), and compound 4 showed a 2D 4-connected (32·62·72) kgm sheet. To our delight, fluorescence measurements showed that compound 1 could selectively and sensitively detect Cr3+ cations and nitrobenzene derivatives (nitrobenzene (NB), p-nitrotoluene (PNT), and p-nitroaniline (PNA)), which suggested that CPs of 1 was a promising bifunctional luminescence sensor material that could sense metal ions and small organic molecules. Moreover, 1 showed excellent photocatalytic activity.

Ruthenium(II)–Arene Metallacycles: Crystal Structures, Interaction with DNA, and Cytotoxicity

A series of 24, 26-membered RuII2 metallamacrocycles containing 1-{3-[(1H-imidazol-1-yl)methyl]benzyl}-1H-imidazole (m-bib) and 1-{4-[(1H-imidazol-1-yl)methyl]benzyl}-1H-imidazole (p-bib) ligands have been synthesized and characteriz

Insights into the Formation and Structures of Molecular Gels by Diimidazolium Salt Gelators in Ionic Liquids or “Normal” Solvents

Insights are provided into the properties of molecular gels formed by diimidazolium salts both in “normal” solvents and ionic liquids. These materials can be interesting for applications in green and sustainable chemistry in which ionic liquids play a sig

Anti-anti-sulfuration recovery agent 1,3-bis ( lemon rice polishings imide methyl) benzene preparation method

The invention discloses a method for preparing anti-vulcanization reversion agent 1,3-bis(citraconimidomethyl)benzene. The method comprises the following steps: mixing itaconic acid, dimethylsulfoxide and disodium hydrogen phosphate according to a ratio, raising the temperature to be 175-195 DEG C, keeping the temperature and reacting for 1-2 hours, removing a solvent, subsequently dehydrating so as to prepare liquid 2-methyl maleic anhydride, further mixing 2-methyl maleic anhydride, m-xylylenediamine, xylene and pyridine according to a ratio, performing reaction under reflux for 3-4 hours at 120 DEG C, distilling under reduced pressure to obtain a crude product, finally recrystallizing the crude product, cooling down, filtering and drying so as to obtain 1,3-bis(citraconimidomethyl)benzene. As no acetic anhydride is used, no acetic acid is generated in the process, so that corrosion on equipment and environmental pollution are greatly reduced; in addition, the product prepared by using the method is high in yield and good in purity, and no equipment needs to be additionally arranged, so that the method is high in practicability.

ZINC COMPLEX

A zinc complex characterized in exhibiting an octahedral structure and being configured from repeating units represented by general formula (I): wherein L represents a linker region, and R1 represents a C1-4 alkyl group, which can have a halogen atom.

Distinct structures of inorganic-organic supramolecular assemblies based on discrete metallocyclic complexes incorporating flexible imidazole ligands: Syntheses, crystal structures and properties

Three new interesting discrete dinuclear metallocyclic complexes, namely, {[Pd2(1)4](NO3)4· 2DMSO· 2H2O}n (4), [Pd2(2) 2Br4]n (5), and {[Pd2(3) 2Cl4]·4DMSO}n (6) have been successfully synthesized by the reaction of flexible exo-bidentate imidazole-containing ligands 1, 3-bis(imidazol-1-ylmethyl)benzene (1), 1, 3-bis(imidazol-1-ylmethyl)- 5-methylbenzene (2), and 2, 6-bis(imidazol-1-ylmethyl)-4-tert-butyl-phenol (3) with corresponding palladium salts. All these complexes were characterized by NMR spectroscopy in combination with elemental analysis, powder X-ray diffraction (PXRD), single-crystal X-ray diffraction, and thermal gravimetric analysis (TGA), respectively. Though all three complexes involve the similar supramolecular building blocks [2+2] metallocyclic units, under the inducement effect of the organic ligands, compounds 4-6 exhibit delicate geometric diversification of the resulting high-dimensional inorganic-organic supramolecular assemblies (e.g., [4+2] lantern-like cage structure, 1D channel, and 2D undulating framework, respectively). Furthermore, these results demonstrate that the secondary interactions such as intermolecular π ··· π stacking interactions and hydrogen bonds could play important roles in the aspect of linking low-dimensional entities into high-dimensional supramolecular frameworks.

Ag(I)-N-heterocyclic carbene complexes of N-allyl substituted imidazol-2-ylidenes with ortho-, meta- and para-xylyl spacers: Synthesis, crystal structures and in vitro anticancer studies

A series of N-allyl substituted xylyl-linked imidazolium salts (7-10) and their respective Ag(I)-N-heterocyclic carbene (NHC) complexes (11-14) have been synthesized and characterized by a number of spectral and analytical techniques. Molecular structure of complexes 13 and 14 were established by single-crystal X-ray diffraction method. The in vitro anticancer activity of all imidazolium salts and their Ag(I)-carbene complexes were investigated using human colorectal (HCT 116) cancer cell lines. Imidazolium salts displayed no activity for HCT 116 cell lines, except for 9; yielding IC50 value of 15.9 μM. Ag(I)-carbene complexes 12-14 showed exceptionally good activity (0.9-1.3 μM) against tested cancer cell lines. Furthermore, complex 11 displayed relatively good anticancer activity with IC50 value of 5.2 μM, which is almost equal to standard used.

AN ANTIMICROBIAL COMPOSITION

The present disclosure relates to an antimicrobial composition comprising at least one polymer or oligomer, the polymer and oligomer being comprised of repeating units of hydrophilic heterocyclic amine monomers that are coupled by hydrophobic linkers selected to confer the antimicrobial activity to the composition, methods of producing the same and uses of the antimicrobial composition.