Month: October 2022

Quality Control of 2-Bromo-1H-imidazoleIn 2021 ,《Template-Mediated Control over Polymorphism in the Vapor-Assisted Formation of Zeolitic Imidazolate Framework Powders and Films》 was published in Angewandte Chemie, International Edition. The article was written by Tu, Min; Kravchenko, Dmitry E.; Xia, Benzheng; Rubio-Gimenez, Victor; Wauteraerts, Nathalie; Verbeke, Rhea; Vankelecom, Ivo F. J.; Stassin, Timothee; Egger, Werner; Dickmann, Marcel; Amenitsch, Heinz; Ameloot, Rob. The article contains the following contents:

The landscape of possible polymorphs for some metal-organic frameworks (MOFs) can pose a challenge for controlling the outcome of their syntheses. Demonstrated here is the use of a template to control in the vapor-assisted formation of zeolitic imidazolate framework (ZIF) powders and thin films. Introducing a small amount of either ethanol or DMF vapor during the reaction between ZnO and 4,5-dichloroimidazole vapor results in the formation of the porous ZIF-71 phase, whereas other conditions lead to the formation of the dense ZIF-72 phase or amorphous materials. Time-resolved in situ small-angle X-ray scattering reveals that the porous phase is metastable and can be transformed into its dense polymorph. This transformation is avoided through the introduction of template vapor. The porosity of the resulting ZIF powders and films was studied by N2 and Kr physisorption, as well as positron annihilation lifetime spectroscopy. The templating principle was demonstrated for other members of the ZIF family as well, including the ZIF-7 series, ZIF-8_Cl, and ZIF-8_Br. In addition to this study using 2-Bromo-1H-imidazole, there are many other studies that have used 2-Bromo-1H-imidazole(cas: 16681-56-4Quality Control of 2-Bromo-1H-imidazole) was used in this study.

2-Bromo-1H-imidazole(cas: 16681-56-4) is a member of imidazole. Its exclusive structural characteristics with enviable electron-rich features are favorable for imidazole-based fused heterocycles to bind efficiently with an array of enzymes and receptors in biological systems through various weak interactions like hydrogen bonds, ion-dipole, cation-π, π-π stacking, coordination, Van der Waals forces, hydrophobic effects, etc., and therefore they demonstrate widespread bioactivities. Quality Control of 2-Bromo-1H-imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Correction: Substituent effects on the basicity (pKa) of aryl guanidines and 2-(arylimino)imidazolidines: correlations of pH-metric and UV-metric values with predictions from gas-phase ab initio bond lengths [Erratum to document cited in CA168:305952]》 was published in New Journal of Chemistry in 2017. These research results belong to Dardonville, Christophe; Caine, Beth A.; Navarro de la Fuente, Marta; Martin Herranz, Guillermo; Corrales Mariblanca, Beatriz; Popelier, Paul L. A.. Synthetic Route of C6H10N2O2S The article mentions the following:

In the original publication, there are errors in the acknowledgments section; the correction is provided here. In the experiment, the researchers used many compounds, for example, Methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate(cas: 60546-77-2Synthetic Route of C6H10N2O2S)

Methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate(cas: 60546-77-2) belongs to imidazoles.Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine. Synthetic Route of C6H10N2O2S In addition, imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Synthesis, thermal stability, vibrational spectra and conformational studies of novel dicationic meta-xylyl linked bis-1-methylimidazolium ionic liquids》 was written by Boumediene, Mostefa; Haddad, Boumediene; Paolone, Annalisa; Drai, Mokhtar; Villemin, Didier; Rahmouni, Mustapha; Bresson, Serge; Abbas, Ouissam. Formula: C4H6N2This research focused onxylyl methylimidazolium ionic liquid thermal stability IR Raman spectra. The article conveys some information:

In recent years, dicationic ionic liquids have been subject of a strongly growing research effort for their interesting and important properties that suggest them to be potential candidate for many applications. Therefore, the knowledge about the synthesis, thermal stability, vibrational spectra and conformational behavior of these compounds is an important subject of study. The objective of the work presented in this paper is to investigate the influence of the substituent relative meta-position of dicationic ionic liquids (ILs), namely meta-xylyl linked bis-1-methylimidazolium ILs, on thermal stability, vibrational spectra and conformational studies. The obtained dicationic ILs were characterized by 1H NMR, 13C NMR, 19F NMR, 31P NMR and FT-IR spectroscopy. Also, their thermal properties were determined and compared. The thermal behavior confirmed that [m-C6H4(CH2ImMe)2+] dicationic ILs containing [(CF3SO2)2N-]2 and [PF6-]2 are more stable that the dichloride [Cl-]2, and bis(tetrafluoroborate) [BF4-]2 dicationic ILs, and they show a good thermal stability up to 340 °C which makes them suitable for thermal application. In the next step, a computational study of the conformers of [m-C6H4(CH2ImMe)2+], by means of DFT calculations with the 6-31G** basis set and the B3LYP theory was performed. Addnl., vibrational spectroscopy studies were conducted by IR (FTIR) and Raman (FT-Raman) spectroscopy on the four dicationic ILs, differing for their anions. Finally a computational investigation of the interactions between anions and cation is presented. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazole(cas: 616-47-7Formula: C4H6N2)

1-Methyl-1H-imidazole(cas: 616-47-7) is used as a precursor for the synthesis of pyrrole-imidazole polyamides, ionic liquids such as 1-butyl-3-methylimidazolium hexafluorophosphate.Formula: C4H6N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Versatile and Highly Efficient trans-[Pd(NHC)Cl2(DMS/THT)] Precatalysts for C-N and C-C Coupling Reactions in Green Solvents》 was written by Liu, Yaxu; Voloshkin, Vladislav A.; Scattolin, Thomas; Peng, Min; Van Hecke, Kristof; Nolan, Steven P.; Cazin, Catherine S. J.. Product Details of 258278-25-0 And the article was included in European Journal of Organic Chemistry on April 12 ,2022. The article conveys some information:

A straightforward synthetic procedure to well-defined, air- and moisture- stable trans-[Pd(NHC)Cl2(DMS/THT)] (NHC=IPr, SIPr, IMes, IPrCl, IPr*, IPr#) pre-catalysts was reported. These complexes were obtained by reacting NHC.HCl imidazolium salts with trans-[PdCl2(DMS/THT)2] precursors with the assistance of the weak base K2CO3 in green acetone at40°C. The scalability of this protocol was demonstrated. The catalytic activity of the synthesized complexes was studied in the Buchwald-Hartwig and Suzuki-Miyaura reactions. Remarkably, most of the synthesized complexes exhibited higher catalytic activity with respect to their PEPPSI congeners in the Buchwald-Hartwig amination in 2-MeTHF. In particular, complex trans-[Pd(IPr#)Cl2(DMS)] enabled the coupling of various (hetero)aryl chlorides and primary/secondary amines with a 0.2 mol% catalyst loading. In addition, trans-[Pd(IPr)Cl2(DMS)] showed excellent performance in the room-temperature Suzuki-Miyaura reaction involving various (hetero)aryl chlorides and aryl boronic acids. In summary, the synthesized complexes, especially trans-[Pd(NHC)Cl2(DMS)], was considered as greener alternatives to classical PEPPSI type catalysts based on the lower toxicity of the throw-away DMS ligand compared to 3-chloropyridine. In the experimental materials used by the author, we found 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Product Details of 258278-25-0)

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) may be used as a precursor to the free carbene 1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene, and also used as an in situ formed catalyst in a variety of reactions, e.g. amination, Heck coupling reaction, the ring-opening metathesis polymerization (ROMP), hydrogenation.Product Details of 258278-25-0In addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of C27H39ClN2On September 30, 2020 ,《Quinolinyl Imidazolidin-2-imine Nickel Catalyzed Efficient Copolymerization of Norbornene with para-Chlorostyrene》 was published in Chinese Journal of Polymer Science. The article was written by Li, Yan-Qing; Zhou, Jian; Xiao, Ru; Cai, Zheng-Guo. The article contains the following contents:

A series of novel quinolinyl imidazolidin-2-imine nickel complexes with different substituents on the imidazolidin-2-imine ligand were synthesized and characterized. The complexes in the presence of methylaluminoxane (MAO) as a cocatalyst catalyzed the copolymerization of norbornene (N) and styrene (S) or para-chlorostyrene (CS) with high activity (up to 1070 kg·mol-1·h-1). The installation of sterically bulky substituents on the imidazolidine-2-imine ligand was effective for the increase of the mol. weight and the comonomer content, affording high mol. weight copolymers with tunable CS content (0.57 mol%-11.7 mol%), in which the existence of Cl group can provide reaction site for the further functionalization of copolymers as well as the synthesis of graft or crosslinked polymers. The linear relationship between the comonomer content and the glass transition temperature of the copolymers and the monomer reactivity ratios in the copolymerization indicated the formation of the expected functionalized cyclic olefin copolymers (COC). In the experiment, the researchers used 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Synthetic Route of C27H39ClN2)

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) may be used as a precursor to the free carbene 1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene, and also used as an in situ formed catalyst in a variety of reactions, e.g. amination, Heck coupling reaction, the ring-opening metathesis polymerization (ROMP), hydrogenation.Synthetic Route of C27H39ClN2In addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2014,Chemistry – A European Journal included an article by Morozov, Oleg S.; Lunchev, Andrey V.; Bush, Alexander A.; Tukov, Aleksandr A.; Asachenko, Andrey F.; Khrustalev, Victor N.; Zalesskiy, Sergey S.; Ananikov, Valentine P.; Nechaev, Mikhail S.. Product Details of 852445-84-2. The article was titled 《Expanded-Ring N-Heterocyclic Carbenes Efficiently Stabilize Gold(I) Cations, Leading to High Activity in π-Acid-Catalyzed Cyclizations》. The information in the text is summarized as follows:

Six- and seven-membered expanded-ring N-heterocyclic carbene (er-NHC) Au(I) complexes were synthesized using different synthetic approaches. Complexes with weakly coordinating anions [(er-NHC)AuX] (X- = BF4-, NTf2-, OTf-) were generated in solution According to their 13C NMR spectra, the ionic character of the complexes increases in the order X- = Cl- < NTf2- < OTf- < BF4-. Addnl. factors for stabilization of the cationic complexes are expansion of the NHC ring and the attachment of bulky substituents at the N atoms. These er-NHCs are bulkier ligands and stronger electron donors than conventional NHCs as well as phosphines and sulfides and provide more stabilization of [(L)Au+] cations. A comparative study was carried out of the catalytic activities of five-, six-, and seven-membered carbene complexes [(NHC)AuX], [(Ph3P)AuX], [(Me2S)AuX], and inorganic compounds of Au in model reactions of indole and benzofuran synthesis. Increased ionic character of the complexes was correlated with increased catalytic activity in the cyclization reactions. As a result, the authors developed an unprecedentedly active monoligand cationic [(THD-Dipp)Au]BF4 (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydrodiazepin-2-ylidene Au(I) tetrafluoroborate) catalyst bearing seven-membered-ring carbene and bulky Dipp substituents. Quant. yields of cyclized products were attained in several minutes at room temperature at 1 mol % catalyst loadings. The exptl. observations were rationalized and fully supported by DFT calculations In the part of experimental materials, we found many familiar compounds, such as Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)(cas: 852445-84-2Product Details of 852445-84-2)

Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)(cas: 852445-84-2) belongs to imidazoles.Imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies.
However, the application of imidazoles is not limited to the field of peptides and peptidomimetics. Product Details of 852445-84-2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2009,Guillemont, Jerome; Benjahad, Abdellah; Oumouch, Said; Decrane, Laurence; Palandjian, Patrice; Vernier, Daniel; Queguiner, Laurence; Andries, Koen; de Bethune, Marie-Pierre; Hertogs, Kurt; Grierson, David S.; Nguyen, Chi Hung published 《Synthesis and Biological Evaluation of C-5 Methyl Substituted 4-Arylthio and 4-Aryloxy-3-Iodopyridin-2(1H)-one Type Anti-HIV Agents》.Journal of Medicinal Chemistry published the findings.HPLC of Formula: 16681-56-4 The information in the text is summarized as follows:

A series of C-5 Me substituted 4-arylthio- and 4-aryloxy-3-iodopyridin-2(1H)-ones, e.g. I (X = O, S; R = SCH2CONHMe, 2-tetrazolyl, 1-imidazolyl, etc.), has been synthesized as new pyridinone analogs for their evaluation as anti-HIV inhibitors. The optimization at the 5-position was developed through an efficient use of the key intermediates 5-ethoxycarbonyl- and 5-cyano-pyridin-2(1H)-ones. Biol. studies revealed that several compounds show potent HIV-1 reverse transcriptase inhibitory properties, for example, I [X = S; R = 1-tetrazolyl, 2-tetrazolyl] are active at 0.6-50 nM against wild type HIV-1 and a panel of major simple/double HIV mutant strains. The experimental part of the paper was very detailed, including the reaction process of 2-Bromo-1H-imidazole(cas: 16681-56-4HPLC of Formula: 16681-56-4)

2-Bromo-1H-imidazole(cas: 16681-56-4) is a member of imidazole. Its exclusive structural characteristics with enviable electron-rich features are favorable for imidazole-based fused heterocycles to bind efficiently with an array of enzymes and receptors in biological systems through various weak interactions like hydrogen bonds, ion-dipole, cation-π, π-π stacking, coordination, Van der Waals forces, hydrophobic effects, etc., and therefore they demonstrate widespread bioactivities. HPLC of Formula: 16681-56-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2017,Gund, Dnyandev Radhu; Tripathi, Alok Pramod; Vaidya, Sanjay Dashrath published 《Synthesis and antimicrobial activity of some novel N-substituted benzimidazoles》.European Journal of Chemistry published the findings.Name: 2-Chloro-1H-benzo[d]imidazole The information in the text is summarized as follows:

Synthesis of a series of new substituted benzimidazole derivatives by the condensation of o-phenylenediamine with urea to give 1,3-dihydro-benzimidazol-2-one which reacted with phosphoryl chloride to give 2-chloro-1H-benzimidazole is reported. The product was then alkylated at the benzimidazole NH with different electrophilic reagents leading to functionalized derivatives Structures of the newly synthesized products have been deduced on the basis of spectral and anal. data. The synthesized compounds were screened for their antimicrobial activity. This exhibited some promising results towards testing organism in-vitro. The results came from multiple reactions, including the reaction of 2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1Name: 2-Chloro-1H-benzo[d]imidazole)

2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1) binds to monoclonal antibodies, inhibiting their binding to their corresponding antigens. This activity may be due to its ability to bind covalently with amino groups on proteins and other molecules.Name: 2-Chloro-1H-benzo[d]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2017,Jiang, Kun-Ming; Zhang, Jian-Qiang; Jin, Yi; Lin, Jun published 《1,3-Dipolar Cycloaddition of Imidazole Derivatives with Nitrile Oxide: Synthesis of Imidazo[1,2,4]oxadiazole Derivatives》.Asian Journal of Organic Chemistry published the findings.Name: 2-Chloro-1H-benzo[d]imidazole The information in the text is summarized as follows:

A concise and efficient synthesis of imidazo[1,2,4]oxadiazole derivatives I [R1 = Ph, 4-FC6H4, 4-MeOC6H4, etc.; R2 = H, 6,7-di-Me] that proceeded through the [3+2] cycloaddition of 2-chloro-1H-benzo[d]imidazole with nitrile oxides was developed. This strategy conveniently constructed tricyclic imidazole heterocyclic derivatives that contained a broad range of functional groups. Compound I [R1 = 4-ClC6H4; R2 = 6,7-di-Me] showed excellent cytotoxic activity against the KYSE410 cell line (IC50 = 0.26 μM). The compounds I were promising candidates for drug discovery. In the experimental materials used by the author, we found 2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1Name: 2-Chloro-1H-benzo[d]imidazole)

2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1) binds to monoclonal antibodies, inhibiting their binding to their corresponding antigens. This activity may be due to its ability to bind covalently with amino groups on proteins and other molecules.Name: 2-Chloro-1H-benzo[d]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2019,Colloids and Surfaces, B: Biointerfaces included an article by Tan, Yulong; Leonhard, Matthias; Moser, Doris; Ma, Su; Schneider-Stickler, Berit. Recommanded Product: 934-32-7. The article was titled 《Antibiofilm efficacy of curcumin in combination with 2-aminobenzimidazole against single- and mixed-species biofilms of Candida albicans and Staphylococcus aureus》. The information in the text is summarized as follows:

Mixed fungal and bacterial biofilm associated infections of implants have been a huge challenge in health care because of the increased resistance to antimicrobials and the critical biol. differences between fungi and bacteria. In this study, we evaluated the 2-aminobenzimidazole (2ABI) and curcumin (CUR) alone to inhibit planktonic cell growth, adhesion as well as single and mixed species biofilms of Candida albicans and Staphylococcus aureus on silicone. The combined effects between 2ABI and CUR on mixed species biofilm formation and pre-formed biofilm were assessed. Our work showed that 2ABI or CUR alone was effective as a sole agent, inhibiting planktonic growth, adhesion and the biofilm formation of bacteria and fungi on the silicone surface. The combination of 2ABI and CUR exhibited the enhanced effect on mixed biofilm compared to mono-drug therapy. The biofilm architecture was investigated by SEM (SEM) and the distinction of living/dead organisms within biofilm was examined by confocal laser scanning microscopy (CLSM). The combination activity was most potent on mixed biofilm. These results suggest the potential applicability of 2ABI and CUR to treatment of biofilm related device infections. The results came from multiple reactions, including the reaction of 1H-Benzo[d]imidazol-2-amine(cas: 934-32-7Recommanded Product: 934-32-7)

1H-Benzo[d]imidazol-2-amine(cas: 934-32-7) can be used in the hydrolysis of a choline carbonate. It was also used in the synthesis of imidazo[1,2-a]benzimidazoles.Recommanded Product: 934-32-7

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem