Month: October 2022

Reference of Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)On September 22, 2010 ,《C-C Coupling Reactivity of an Alkylgold(III) Fluoride Complex with Arylboronic Acids》 was published in Journal of the American Chemical Society. The article was written by Mankad, Neal P.; Toste, F. Dean. The article contains the following contents:

Previously, alkylgold(III) fluorides are proposed as catalytic intermediates that undergo C-C coupling with reagents such as arylboronic acids in Au(I)/Au(III) cross-coupling reactions. Here is reported the first exptl. evidence for this elementary mechanistic step. Complexes of the type (NHC)AuMe (NHC = N-heterocyclic carbene) were oxidized with XeF2 to yield cis-(NHC)AuMeF2 products, which are in equilibrium with their fluoride-dissociated, dimeric [(NHC)AuMe(μ-F)]2[F]2 forms. In one case, a monomeric cis-(NHC)AuMeF2 complex was favored exclusively in solution, and it reacts with a variety of ArB(OH)2 reagents to yield Ar-CH3 products. In the experimental materials used by the author, we found Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)(cas: 852445-84-2Reference of Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I))

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 also present in imidazole ring alkaloids, which are potential therapeutics for thrombosis, cancer and inflammatory diseases.Reference of Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I) 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.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Agata, Ryosuke; Takaya, Hikaru; Matsuda, Hiroshi; Nakatani, Naoki; Takeuchi, Katsuhiko; Iwamoto, Takahiro; Hatakeyama, Takuji; Nakamura, Masaharu published an article on February 28 ,2019. The article was titled 《Iron-catalyzed cross coupling of aryl chlorides with alkyl grignard reagents: synthetic scope and Fe(II)/Fe(IV) mechanism supported by X-ray absorption spectroscopy and density functional theory calculations》, and you may find the article in Bulletin of the Chemical Society of Japan.Product Details of 258278-25-0 The information in the text is summarized as follows:

A combination of Fe(III) fluoride and 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene (SIPr) catalyzes the high-yielding cross coupling of an electron-rich aryl chloride with an alkyl Grignard reagent, which cannot be attained using other Fe catalysts. A variety of alkoxy- or amino-substituted aryl chlorides can be cross-coupled with various alkyl Grignard reagents regardless of the presence or absence of β-hydrogens in the alkyl group. A radical probe experiment using 1-(but-3-enyl)-2-chlorobenzene does not afford the corresponding cyclization product, therefore excluding the intermediacy of radical species. Solution-phase x-ray absorption spectroscopy (XAS) anal., with the help of d. functional theory (DFT) calculations, indicates the formation of a high-spin (S = 2) heteroleptic difluorido organoferrate(II), [MgX][Fe(II)F2(SIPr)(Me/alkyl)], in the reaction mixture DFT calculations also support a feasible reaction pathway, including the formation of a difluorido organoferrate(II) intermediate which undergoes a novel Lewis acid-assisted oxidative addition to form a neutral organoiron(IV) intermediate, which leads to an Fe(II)/Fe(IV) catalytic cycle, where the fluorido ligand and the Mg ion play key roles. 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: 258278-25-0Product Details of 258278-25-0)

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.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

Wenzel, Anna G.; Grubbs, Robert H. published their research in Journal of the American Chemical Society on December 20 ,2006. The article was titled 《Ruthenium Metallacycles Derived from 14-Electron Complexes. New Insights into Olefin Metathesis Intermediates》.HPLC of Formula: 866926-59-2 The article contains the following contents:

Ru(IV) metallacycles derived from both ethylene and propene are reported. The propene-derived metallacycles represent the 1st observed examples of substituted ruthenacyclobutanes and offer new insight into the preferred stereochem. orientation about metathesis intermediates. The authors showed evidence supporting the bottom-face orientation of Ru(IV) metallacycles derived from both ethylene and propene. The unsym. disubstituted 1-(2,6-diisopropylphenyl)-3-(2,4,6-trimethylphenyl)-4,5-dihydroimidazolinium chloride ([H2ImesiPrH]+Cl-) and the ruthenium carbene complex [(H2ImesiPr)Ru(:CHPCy3)(Cl)2]+[BF4]- were prepared The mol. structure of the ruthenium carbene complex was determined by x-ray crystallog. Reaction of the ruthenium carbene complex with ethylene gave a ruthenacyclobutane possessing an unsym. N-heterocyclic carbene (NHC) ligand. The complex was studied to ascertain the dynamics of the NHC relative to the metallacycle ring. Ruthenacyclobutanes studied possess exchange cross-peaks between the α- and β-positions in the 2-dimensional NMR, indicating a dynamic structure. The ruthenacyclobutanes derived from ethylene and propene proceed through nonproductive metallacycle formations/cycloreversions prior to olefin exchange. The implications of these results to the mechanism of Ru-catalyzed olefin metathesis are discussed. In the part of experimental materials, we found many familiar compounds, such as 1-(2,6-Diisopropylphenyl)-3-mesityl-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 866926-59-2HPLC of Formula: 866926-59-2)

1-(2,6-Diisopropylphenyl)-3-mesityl-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 866926-59-2) belongs to imidazoles.Imidazole rings are also present in imidazole ring alkaloids, which are potential therapeutics for thrombosis, cancer and inflammatory diseases.HPLC of Formula: 866926-59-2 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.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 1923,King, Harold; Murch, Wm. O. published 《Bromination of glyoxaline-4-carboxanilide》.Journal of the Chemical Society, Transactions published the findings.SDS of cas: 16681-56-4 The information in the text is summarized as follows:

The object of this investigation was the preparation of 4-bromoglyoxaline-5-carboxylic acid (I) with the view of synthesizing xanthine by condensation of the ester with CO(NH2)2. The acid was obtained but the small yields have prevented attempts at the condensation. Two mols. Br react with glyoxaline-4-carboxanilide in glacial AcOH, giving a mixture of mono-, di- and tri-Br derivatives This is extracted with H2O on the boiling H2O bath. The aqueous solution deposits glyoxaline-4-carbox-p-bromoanilide, crystallizing from AcOH with 2 AcOH of crystallization, lost at 100° and then m. 273-4°. Hydrolysis gives I. 5-Bromoglyoxaline-4-carbox-p-bromoanilide (II), m. 245-6°, is then extracted with very dilute HCl. The residue is the 2,5-dibromo derivative (III), C10H6ON3Br3, which crystallines with 1 C2H4O2, and m. 257-8° (decomposition). Hydrolysis of III with HCl (sealed tube at 150° for 3 hrs.) gave p-BrC6H4NH2, and a mixture containing about 95% dichloro- and 5% dibromoglyoxaline, m. 184-5°. Hydrolysis of III with HBr gave a mixture of the 2,5-Br2 derivative and 2-bromoglyoxaline, m. 207°; Pauly’s reagent gives a deep orange color; picrate, yellow, m. 232° (decomposition); nitrate, decomposes violently 137°. 2,5-Dibromoglyoxaline nitrate-silver nitrate, 2C3H2N2Br2.AgNO3.HNO3. II is soluble in about 6 parts boiling AcOH. It is mixed with a very small amount of a compound containing about 50% Br and m. 247°. Hydrolysis of II with 24% HBr gives p-BrC6H4NH2 and 5-bromoglyoxaline-4-carboxylic acid, m. 265°, soluble in 50 parts boiling H2O, and forms a hydrochloride, nitrate, Ag salt, and gives a deep orange color with Pauly’s reagent. Et ester, m. 170-1°. With 30% HBr some 4-bromoglyoxaline was also isolated. Bromination of II gave III with some of the compound m. 247°. The results came from multiple reactions, including the reaction of 2-Bromo-1H-imidazole(cas: 16681-56-4SDS of cas: 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. SDS of cas: 16681-56-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2019,Journal of Photochemistry and Photobiology, B: Biology included an article by Li, Ke; Dong, Wenyi; Liu, Qingzhu; Lv, Gaochao; Xie, Minhao; Sun, Xinchen; Qiu, Ling; Lin, Jianguo. Product Details of 58-85-5. The article was titled 《A biotin receptor-targeted silicon(IV) phthalocyanine for in vivo tumor imaging and photodynamic therapy》. The information in the text is summarized as follows:

Phthalocyanines (Pcs) are a kind of potential photosensitizers for fluorescence imaging and photodynamic therapy (PDT). However, the clin. application of Pcs is suffered from their poor solubility, high aggregation tendency and low tumor-specificity. To address these problems, two biotin moieties were linked to the axial positions of silicon(IV) phthalocyanine (SiPc) through hydrophilic polyethylene glycol (PEG) linkers to synthesize a new water-soluble and tumor-targeting photosensitizer (compound 1). The introduction of PEG linkers on SiPc markedly reduced the aggregation tendency of the conjugate. In vitro assays also proved that compound 1 could specifically accumulate in biotin receptor (BR) pos. Hela cells through the BR-mediated internalization. Owing to the good characteristics of water-solubility and low aggregation, the bioactivity of compound 1 was examined in the xenograft tumor model. In vivo imaging and tissue distribution studies showed that compound 1 selectively accumulated in the tumor tissue, with tolerable signals found in other organs of the tumor-bearing mice. Furthermore, compound 1 could significantly depress tumor progression in vivo under irradiation After 14 days of the treatment, the tumor volumes were even smaller than the beginning size. All these results reveal that compound 1 is a promising candidate, with low aggregation tendency, high tumor-specificity and water-solubility, for in vivo tumor diagnosis and PDT treatment.5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid(cas: 58-85-5Product Details of 58-85-5) was used in this study.

5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid(cas: 58-85-5) may be used to elute proteins from avidin/streptavidin resins. It has been used for culturing of oligodendrocytes.Product Details of 58-85-5 The biotin/avidin or biotin/streptavidin interaction is utilized in many labeling and purification schemes.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《A Versatile Electrochemical Batch Reactor for Synthetic Organic and Inorganic Transformations and Analytical Electrochemistry》 was written by Stephen, Hamish R.; Schotten, Christiane; Nicholls, Thomas P.; Woodward, Madeleine; Bourne, Richard A.; Kapur, Nikil; Willans, Charlotte E.. Name: 1,3-Dimesityl-1H-imidazol-3-ium chloride And the article was included in Organic Process Research & Development in 2020. The article conveys some information:

A standardized and versatile electrochem. batch reactor that has wide applicability in both organic and inorganic synthesis and anal. electrochem. was developed. A variety of synthetic electrochem. transformations were performed to showcase the versatility and demonstrate the reactor, including the synthesis of five Cu(I)-NHC complexes, two Au(I)-NHC complexes, and one Fe(II)-NHC complex as well as an Fe(III)-salen complex. The reactor is based on a com. available vial with an adapted lid, making it inexpensive and highly flexible. It features a fixed interelectrode distance, which is crucial for reproducibility, along with the ability to accommodate a variety of interchangeable electrode materials. The reactor also was used in conjunction with a parallel plate, allowing rapid screening and optimization of an organic electrochem. transformation. Cyclic voltammetry was performed within the reactor on a range of imidazolium salt analytes using an external potentiostat. The ability to use this reactor for both anal. and synthetic organic and inorganic chem. is enabled by a flexible and characterizable design. In addition to this study using 1,3-Dimesityl-1H-imidazol-3-ium chloride, there are many other studies that have used 1,3-Dimesityl-1H-imidazol-3-ium chloride(cas: 141556-45-8Name: 1,3-Dimesityl-1H-imidazol-3-ium chloride) was used in this study.

1,3-Dimesityl-1H-imidazol-3-ium chloride(cas: 141556-45-8) is a ligand for arylation of aldehydes and for carbene catalyzed intermolecular arylation of C-H bonds. It is used as a phosphine-free ligand in various metal-catalyzed coupling reactions, often with advantageous results in difficult cases.Name: 1,3-Dimesityl-1H-imidazol-3-ium chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Boehme, Matthias D.; Wilm, Lukas F. B.; Hepp, Alexander; Hahn, F. Ekkehardt published an article in 2021. The article was titled 《Regioselective Double Oxidative Addition of Bis-NHC Precursors》, and you may find the article in European Journal of Inorganic Chemistry.Category: imidazoles-derivatives The information in the text is summarized as follows:

The 4,4′-dimethylenebiphenyl linked sym. bis-(2-chlorobenzimidazole) (1) and the unsym. 2-chlorobenzimidazolium/2-chlorobenzimidazole [2(BF4)] have been reacted with one equiv of [Pd(PPh3)4] in oxidative addition reactions. For the sym. bis-NHC precursor 1, double metalation of both 2-chlorobenzimidazole sites to give the dinuclear bis-pNHC complex ([3][BF4]2) was observed The unsym. compound 2(BF4) was only metalated at the 2-chlorobenzimidazolium site with formation of the mononuclear NHC complex ([4][BF4]). The remaining 2-chlorobenzimidazole moiety was subsequently metalated in a second oxidative addition reaction with [M(PPh3)4] (M = Pd, Pt) to give the homobimetallic NHC/pNHC complex [5](BF4)2 (M = Pd) and the heterobimetallic complex [6](BF4)2 demonstrating the unique site-selective metalation of the bis-NHC precursor 2(BF4) by two consecutive oxidative additions After reading the article, we found that the author used 2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1Category: imidazoles-derivatives)

2-Chloro-1H-benzo[d]imidazole(cas: 4857-06-1) is an analog of benzimidazole that has been synthesized by Langmuir adsorption isotherm. It is a white crystalline solid that can be dissolved in water and hydrochloric acid. 2-Chloro-1H-benzo[d]imidazole inhibits the growth of herpes simplex virus by acting as a competitive inhibitor for the viral enzyme thymidine kinase, which catalyzes the conversion of thymine to thymidine.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2022,Iwamoto, Hiroaki; Ozawa, Yu; Hayashi, Yuta; Imamoto, Tsuneo; Ito, Hajime published an article in Journal of the American Chemical Society. The title of the article was 《Conformationally Fixed Chiral Bisphosphine Ligands by Steric Modulators on the Ligand Backbone: Selective Synthesis of Strained 1,2-Disubstituted Chiral cis-Cyclopropanes》.Reference of 1,3-Dimesityl-1H-imidazol-3-ium chloride The author mentioned the following in the article:

C1-sym. P-chirogenic bisphosphine ligands (R)-5,8-Si-Quinox-tBu3 (Silyl = SiMe3, SiEt3, SiMe2Ph) were developed. The bulky silyl modulators attached to the ligand backbone fix the phosphine substituents to form rigid chiral environments that can be used for substrate recognition. The ligand showed high performances for a Cu(I)-catalyzed asym. borylative cyclopropanation of bulky silyl-substituted allylic electrophiles to afford higher disfavored 1,2-cis-silyl-boryl-cyclopropanes than the other possible isomers, trans-cyclopropane and allylboronate (up to 97% yield; 98% ee; cis/trans = >99:1; cyclopropane/allylboronate = >99:1). Detailed computational studies suggested that the highly rigid phosphine conformation, which is virtually undisturbed by the steric interactions with the bulky silyl-substituted allyl electrophiles, is key to the high stereo- and product-selectivities. Also, the detailed computational anal. provided insight into the mechanism of the stereoretention or -inversion of the chiral alkylcopper(I) intermediate in the intramol. cyclization. In the experiment, the researchers used 1,3-Dimesityl-1H-imidazol-3-ium chloride(cas: 141556-45-8Reference of 1,3-Dimesityl-1H-imidazol-3-ium chloride)

1,3-Dimesityl-1H-imidazol-3-ium chloride(cas: 141556-45-8) is a ligand for arylation of aldehydes and for carbene catalyzed intermolecular arylation of C-H bonds. It is used as a phosphine-free ligand in various metal-catalyzed coupling reactions, often with advantageous results in difficult cases.Reference of 1,3-Dimesityl-1H-imidazol-3-ium chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Category: imidazoles-derivativesIn 2017 ,《Polysubstituted 2-aminoimidazoles as anti-biofilm and antiproliferative agents: Discovery of potent lead》 appeared in European Journal of Medicinal Chemistry. The author of the article were Gill, Rupinder Kaur; Kumar, Virender; Robijns, Stijn C. A.; Steenackers, Hans P. L.; Van der Eycken, Erik V.; Bariwal, Jitender. The article conveys some information:

Most of the human bacterial infections are associated with the biofilm formation and the natural tolerance of biofilms to antibiotics challenges treatment. Because of their low immunity, cancer patients are especially susceptible to bacterial infections. Compounds with anti-biofilm activity could therefore become a useful adjunct to chemotherapy, in particular if they also show antiproliferative activities. Taking this into consideration and as a result of continuous interest in 2-aminoimidazole derivatives, a series of novel polysubstituted 2-aminoimidazoles, e.g. I, was designed and synthesized. The compounds were evaluated against a panel of three bacterial strains for their biofilm and planktonic growth inhibitory activity and most of them show promising results. Furthermore, the synthesized compounds were evaluated against various cancer cell lines and almost all the compounds were found to possess potent antiproliferative activity. The substitution pattern at the C-4 position and the aryl carboxamide ring at the N-1 position have major effects on the biofilm inhibitory and antiproliferative activity. Especially, the introduction of a p-Me group at the carboxamide ring remarkably enhances both the anti-biofilm and antiproliferative activity. Two potent compounds were further studied for their antiproliferative activity and a flow cytometer-based cell cycle experiment was performed, which revealed their capability to induce G2/M phase cell cycle arrest. Based on these results, these two new compounds having potential to target both cancer proliferation and microbial biofilms might be used in single drug monotherapy. The experimental process involved the reaction of 1H-Imidazol-2-amine(cas: 7720-39-0Category: imidazoles-derivatives)

1H-Imidazol-2-amine(cas: 7720-39-0) belongs to anime. Primary amines having a tertiary alkyl group (R3CNH2) are difficult to prepare with most methods but are made industrially by the Ritter reaction. In this method a tertiary alcohol reacts with hydrogen cyanide (HCN) in the presence of a concentrated strong acid; a formamide, RNH―CHO, is formed first, which then undergoes hydrolysis.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

COA of Formula: C8H15BF4N2In 2019 ,《Fabrication of Hierarchical Porous Carbon Frameworks from Metal-Ion-Assisted Step-Activation of Biomass for Supercapacitors with Ultrahigh Capacitance》 appeared in ACS Sustainable Chemistry & Engineering. The author of the article were Chang, Chengshuai; Wang, He; Zhang, Yunqiang; Wang, Shulan; Liu, Xuan; Li, Li. The article conveys some information:

Advancement in the application of biomass-derived carbon is viewed as one of the most important drivers of sustainable and renewable technologies for energy storage. High-performance biochar with a well-defined structure is extremely attractive as a supercapacitor electrode material. Herein, carbon with an ultrahigh capacitance of 682 F/g at 0.2 A/g for biochar materials and remarkable cycling stability was synthesized from Chinese parasol fluff (CPF). Three-dimensional interconnected hierarchical porous carbon was fabricated via a feasible metal-ion-assisted step-activation method from the biomass precursor. CO2 was used to treat the carbonaceous material from CPF after molten KOH activation for pore structure tuning, while Co2+ was selected as the metal ion additive for directing graphitization. In addition to the extremely high capacitance, the as-synthesized carbon also delivered an energy d. of 46.38 W h/kg at a power d. of 300 W/kg in 1-butyl-3-Me imidazolium tetrafluoroborate/acetonitrile (BMIMBF4/AN) electrolyte, which is much better than for most reported biochar materials and about 10 times better than for com. supercapacitors. The current work points out an excellent sustainable source for fabrication of high-performance electrode materials and, more importantly, a feasible design strategy route for improvement of the electrochem. performance of energy storage devices. The experimental part of the paper was very detailed, including the reaction process of 3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate(cas: 174501-65-6COA of Formula: C8H15BF4N2)

3-Butyl-1-methyl-1H-imidazol-3-ium tetrafluoroborate(cas: 174501-65-6) is a member of lonic liquids. Actually, lonic liquids as innovative fluids have received wide attention only during the past two decades. The number of SCI papers published on lonic liquids has exponentially increased from a few in 1996 to >5000 in 2016, exceeding the annual growth rates of other popular scientific areas. COA of Formula: C8H15BF4N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem