Month: October 2022

《Vegetable oil-based thiol-ene/thiol-epoxy resins for laser direct writing 3D micro-/nano-lithography》 was written by Grauzeliene, Sigita; Navaruckiene, Aukse; Skliutas, Edvinas; Malinauskas, Mangirdas; Serra, Angels; Ostrauskaite, Jolita. Electric Literature of C4H6N2This research focused onvegetable oil thiol ene epoxy resin laser direct writing; biobased polymer; click reactions; dual curing; laser direct writing; linseed oil; optical 3D printing; soybean oil; thiol-ene; thiol-epoxy. The article conveys some information:

The use of renewable sources for optical 3D printing instead of petroleum-based materials is increasingly growing. Combinations of photo- and thermal polymerization in dual curing processes can enhance the thermal and mech. properties of the synthesized thermosets. Consequently, thiol-ene/thiol-epoxy polymers were obtained by combining UV and thermal curing of acrylated epoxidized soybean oil and epoxidized linseed oil with thiols, benzene-1,3-dithiol and pentaerythritol tetra(3-mercaptopropionate). Thiol-epoxy reaction was studied by calorimetry. The changes of rheol. properties were examined during UV, thermal and dual curing to select the most suitable formulations for laser direct writing (LDW). The obtained polymers were characterized by dynamic-mech. thermal anal., thermogravimetry, and mech. testing. The selected dual curable mixture was tested in LDW 3D lithog. for validating its potential in optical micro- and nano-additive manufacturing The obtained results demonstrated the suitability of epoxidized linseed oil as a biobased alternative to bisphenol A diglycidyl ether in thiol-epoxy thermal curing reactions. Dual cured thermosets showed higher rigidity, tensile strength, and Young’s modulus values compared with UV-cured thiol-ene polymers and the highest thermal stability from all prepared polymers. LDW results proved their suitability for high resolution 3D printing-individual features reaching an unprecedented 100 nm for plant-based materials. Finally, the biobased resin was tested for thermal post-treatment and 50% feature downscaling was achieved. In the part of experimental materials, we found many familiar compounds, such as 1-Methyl-1H-imidazole(cas: 616-47-7Electric Literature of 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.Electric Literature of C4H6N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Name: 3-(1H-Benzo[d]imidazol-2-yl)propan-1-olOn October 8, 2015 ,《Discovery and Optimization of a Series of Pyrimidine-Based Phosphodiesterase 10A (PDE10A) Inhibitors through Fragment Screening, Structure-Based Design, and Parallel Synthesis》 was published in Journal of Medicinal Chemistry. The article was written by Shipe, William D.; Sharik, Steven S.; Barrow, James C.; McGaughey, Georgia B.; Theberge, Cory R.; Uslaner, Jason M.; Yan, Youwei; Renger, John J.; Smith, Sean M.; Coleman, Paul J.; Cox, Christopher D.. The article contains the following contents:

Screening of a fragment library for PDE10A inhibitors identified a low mol. weight pyrimidine hit with PDE10A Ki of 8700 nM and LE of 0.59. Initial optimization by catalog followed by iterative parallel synthesis guided by X-ray cocrystal structures resulted in rapid potency improvements with minimal loss of ligand efficiency. Compound 15h, with PDE10A Ki of 8.2 pM, LE of 0.49, and >5000-fold selectivity over other PDEs, fully attenuates MK-801-induced hyperlocomotor activity after i.p. dosing. The experimental process involved the reaction of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9Name: 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol)

3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9) 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. Name: 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol 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

Electric Literature of C27H39ClN2On October 5, 2021 ,《Activated Hoveyda-Grubbs Olefin Metathesis Catalysts Derived from a Large Scale Produced Pharmaceutical Intermediate – Sildenafil Aldehyde》 was published in Advanced Synthesis & Catalysis. The article was written by Monsigny, Louis; Piatkowski, Jakub; Trzybinski, Damian; Wozniak, Krzysztof; Nienaltowski, Tomasz; Kajetanowicz, Anna; Grela, Karol. The article contains the following contents:

Two EWG-activated Hoveyda-Grubbs-type ruthenium complexes (Sil-II and Sil-II’) were obtained, characterized, and screened in a set of olefin metathesis reactions. These catalysts were conveniently synthesized from a com. available pharmaceutical building block – Sildenafil aldehyde – in two steps only. Stability and catalytic activity tests disclosed that the bulkier NHC-ligand bearing catalyst Sil-II’ is visibly more stable and productive than its smaller NHC-analog Sil-II. Good application profile of catalyst Sil-II’ was confirmed in a set of diverse metathesis reactions including ring-closing metathesis (RCM) and cross-metathesis (CM) of complex polyfunctional substrates of medicinal chem. interest, including a challenging macrocyclization of the Pacritinib precursor. Compatibility of the new catalyst with various green solvents was checked and metathesis of Sildenafil and Tadalafil-based substrates was successfully conducted in acetone. The mechanism of Sil-II’ initiation has been investigated through kinetic experiments unveiling that the decrease of the steric hindrance of the chelating alkoxy moiety (from iPrO to EtO) favors the interchange initiation pathway over the typical dissociation pathway for other popular 2nd generation Hoveyda-Grubbs catalysts. The results came from multiple reactions, including the reaction of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Electric Literature 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.Electric Literature 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 2019,Organic & Biomolecular Chemistry included an article by Jang, Won Jun; Kang, Byung-Nam; Lee, Ji Hun; Choi, Yoon Mi; Kim, Chong-Hyeak; Yun, Jaesook. Name: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride. The article was titled 《NHC-copper-thiophene-2-carboxylate complex for the hydroboration of terminal alkynes》. The information in the text is summarized as follows:

An air-stable N-heterocyclic carbene-copper thiophene-2-carboxylate (CuTC) complex has been prepared for the stereoselective hydroboration of terminal alkynes using pinacolborane (HBpin) or 1,8-naphthalenediaminatoborane (HBdan). The newly synthesized complex can be directly activated by hydroboranes without a cocatalyst such as a base, and exhibits high reactivity for the hydroboration of alkynes under mild conditions. A gram-scale hydroboration of terminal phenylacetylene demonstrated the applicability of the copper complex for the preparation of alkenyl boronates. In addition to this study using 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, there are many other studies that have used 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Name: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride) was used in this study.

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) has been employed in an efficient, one-pot synthesis of N-heterocyclic carbene-allylpalladium complexes.Name: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chlorideIn addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Spiridonov, Kirill A.; Kozinenko, Vitaly P.; Nikovsky, Igor A.; Pavlov, Alexander A.; Vol′khina, Tatyana N.; Nelyubina, Yulia V.; Kiryutin, Alexey S.; Yurkovskaya, Alexandra V.; Polezhaev, Alexander A.; Novikov, Valentin V.; Ivanov, Konstantin L. published an article in Mendeleev Communications. The title of the article was 《Phosphite-containing iridium polarization transfer catalysts for NMR signal amplification by reversible exchange》.Application In Synthesis of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride The author mentioned the following in the article:

Two new iridium complexes with an N-heterocyclic carbine and phosphite ligands have been synthesized and characterized. Bubbling of parahydrogen through their solutions resulted in the formation of several hydride complexes. In the presence of pyridine, this process is accompanied by transfer of spin order from the mol. hydrogen to pyridine mols. undergoing dynamic exchange between free and complex-bound states. In the experiment, the researchers used many compounds, for example, 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Application In Synthesis of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride)

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) has been employed in an efficient, one-pot synthesis of N-heterocyclic carbene-allylpalladium complexes.Application In Synthesis of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chlorideIn addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2003,Weiss, Andre; Barba, Victor; Pritzkow, Hans; Siebert, Walter published 《Synthesis, structures and reactivity of macrocyclic imidazolylboranes》.Journal of Organometallic Chemistry published the findings.Application In Synthesis of 2-Bromo-1H-imidazole The information in the text is summarized as follows:

New macrocyclic substituted imidazolylboranes [(imidazol-1-yl)BR12]n, where n = 4 or 5, were obtained from 1-trimethylsilylimidazoles and haloboranes XB(R1)2 by boron/silicon exchange starting from 2-bromoimidazole and benzimidazole. Reaction of 2-bromo-1-trimethylsilylimidazole with H2BCl gave cyclic [C3H2BrN2-BH2]4 (2d) whereas the condensation of unsubstituted 2-bromoimidazole with H2BCl gave dihydroboratobis(2-bromo-3-imidazolium) chloride (3d), which can be converted to 2d by reaction with excess of BH3·THF. Benzimidazole was converted to analogous tetramer [C7H5N2-BH2]4 (2e) by the same reaction sequence via dihydroboratobis(3-benzimidazolium) chloride intermediate (3e). Condensation of 1-trimethylsilylimidazole with R1BCl2 afforded chloro-containing macrocycles [C3H3N2-BClR1]n (2f, 2g’; R1 = iPr2N, H; n = 4, 5, resp.). These macrocycles are formally zwitterionic and contain imidazolyl rings linked through their nitrogen atoms by BH2, B(R1)2 or BR1X units. Despite the steric demand of these derivatives tetrameric macrocycles are formed. The x-ray structures of 2d and 3d, and also of [C3H3N2-BH2]4 (2a), [C3H3N2-BH2]5 (2a’) and [C3H3N2-BMe2]4 (2b) are reported. In the experimental materials used by the author, we found 2-Bromo-1H-imidazole(cas: 16681-56-4Application In Synthesis of 2-Bromo-1H-imidazole)

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. Application In Synthesis of 2-Bromo-1H-imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2018,Mortada, Boushra; Chaplais, Gerald; Veremeienko, Vasyl; Nouali, Habiba; Marichal, Claire; Patarin, Joel published 《Energetic performances of ZIF-8 derivatives: Impact of substitution (Me, Cl, or Br) on imidazolate linker》.Journal of Physical Chemistry C published the findings.Product Details of 16681-56-4 The information in the text is summarized as follows:

The energetic performances of three isomorphic ZIF materials, i.e., ZIF-8_CH3 (Basolite Z1200), ZIF-8_Cl, and ZIF-8_Br, of SOD topol. are studied with high-pressure intrusion-extrusion experiments using water and aqueous electrolyte solutions (KCl 4 M and LiCl 20 M) as nonwetting liquids This work represents an important progress in the field of energetic applications, as the “”ZIF-8_Cl-LiCl 20 M”” system exhibits a spring behavior with a stored energy of 77 J g-1. To the best of our knowledge, this is the highest value for the stored energy obtained using intrusion-extrusion experiments Exptl. results reveal that the intrusion pressure increases with the addition of electrolytes. The systems evolve from a bumper to a shock-absorber or spring behavior with the decrease in the strength of the interactions between the cation of the salt and the imidazolate linker. This explains the bumper or rather the shock-absorber behavior observed for the “”ZIF-8_Br-KCl 4 M”” and “”ZIF-8_CH3-LiCl 20 M”” systems compared to the spring behavior observed with the other systems reported in this work. In the experimental materials used by the author, we found 2-Bromo-1H-imidazole(cas: 16681-56-4Product Details of 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. Product Details of 16681-56-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem