Month: January 2023

Reactions of 4-halo- and 4-methylthio-imidazolium salts with sulfide and methanethiolate ions was written by Begtrup, Mikael. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1979.Application In Synthesis of 4-Bromo-1-methylimidazole This article mentions the following:

The chloroimidazolium salts I [R = H (II), Ph, R¹ = Cl, X = 4-MeC₆H₄SO₃] reacted with Na₂S-NaH to give the ring cleaved products MeNHC(S)CH₂NMeCOR (III; R = H, Ph) and with MeSH-NaH to give the substituted products I [R = H (IV), Ph, R¹ = SMe, X = Cl]; further treatment of IV with MeSH-NaH gave the thione V (R = SMe) and after treatment with NaBr, I (R = R¹ = H, X = Br). The bromo analog I (R = H, R¹ = Br, X = 4-MeC₆H₄SO₃) (VI) reacted with excess Na₂S-NaH to give 67% V (R = H) and with 1 mol equiv to give 42% I (R = R¹ = H, X = Br), together with V (R = H) and III (R = H); similar treatment of I (R = Ph, R¹ = Br, X = 4-MeC₆H₄SO₃) gave 77% I (R = Ph, R¹ = H, X = Br). In the Cl series, thiation predominated over ring cleavage, V (R = Cl) being formed when II was treated with Na₂S-S. When VI was subjected to similar treatment, reduction with formation of I (R = R¹ = H, X = Br) and V (R = H) prevailed over thiation to V (R = Br). Treatment of VI with MeSH-NaH (1 mol equiv) gave 82% I (R = R¹ = H, X = Br) whereas with excess MeS^–, V (R = H) was obtained. In the experiment, the researchers used many compounds, for example, 4-Bromo-1-methylimidazole (cas: 25676-75-9Application In Synthesis of 4-Bromo-1-methylimidazole).

4-Bromo-1-methylimidazole (cas: 25676-75-9) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Application In Synthesis of 4-Bromo-1-methylimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis of new ¹⁸F-radiolabeled silicon-based nitroimidazole compounds was written by Joyard, Yoann;Azzouz, Rabah;Bischoff, Laurent;Papamicael, Cyril;Labar, Daniel;Bol, Anne;Bol, Vanessa;Vera, Pierre;Gregoire, Vincent;Levacher, Vincent;Bohn, Pierre. And the article was included in Bioorganic & Medicinal Chemistry in 2013.Formula: C5H5N3O4 This article mentions the following:

The syntheses of new nitroimidazole compounds using silicon-[¹⁸F]fluorine chem. for the potential detection of tumor hypoxia are described. [¹⁸F]silicon-based compounds were synthesized by coupling 2-nitroimidazole with silyldinaphtyl or silylphenyldi-tert-Bu groups and labeled by fluorolysis or isotopic exchange. Dinaphtyl compounds (6, 10) were labeled in 56-71% yield with a specific activity of 45 GBq/μmol, however these compounds ([¹⁸F]7 and [¹⁸F]11) were not stable in plasma. Phenyldi-tert-Bu compounds were labeled in 70% yield with a specific activity of 3 GBq/μmol by isotopic exchange, or in 81% yield by fluorolysis of siloxanes with a specific activity of 45 GBq/μmol. The labeled compound [¹⁸F]18 was stable in plasma and excreted by the liver and kidneys in vivo. In conclusion, the fluorosilylphenyldi-tert-Bu (SiFA) group is more stable in plasma than fluorosilyldiphenyl moiety. Thus, compound [¹⁸F]18 is suitable for further in vivo assessments. In the experiment, the researchers used many compounds, for example, 2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7Formula: C5H5N3O4).

2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Formula: C5H5N3O4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Self-segregated nano-structure in room temperature ionic liquids was written by Pontoni, Diego;Haddad, Julia;Di Michiel, Marco;Deutsch, Moshe. And the article was included in Soft Matter in 2017.Category: imidazoles-derivatives This article mentions the following:

The nano-segregated bulk structure, and its evolution with the cation’s alkyl length n, are studied by X-ray scattering for an unprecedentedly broad homologous series of a model room-temperature ionic liquid, [C_nMIM][NTf₂] (n = 4-22). A tri-periodic local structure is found, with the lateral periodicities, d_II and d_III independent of n, and a longitudinal one, d_I, linearly increasing with n. The results are consistent with a local structure comprising alternating layers of polar head-groups and apolar, interdigitated, partly overlapping, cations’ alkyl tails, of an average macroscopic mass d. close to that of liquid alkanes. A slope decrease in the linear d_I(n) suggests a change from a lower to a higher rate of increase with n of chain overlap for n â‰?12. The order decay lengths of the layering, and of the lateral chain packing, increase with n, as expected from the increasing van der Waals interaction’s domination of the structure. The head-groups lateral packing decay length decreases with n, due to increasing frustration between the longer lateral periodicity preferred by the head-groups, and the shorter lateral periodicity preferred by the chains. A comparison of the bulk and surface structures highlights the surface’s ordering effect, which, however, does not induce here a surface phase different from the bulk, as it does in liquid crystals and liquid alkanes. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Category: imidazoles-derivatives).

3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5) belongs to imidazole derivatives. Imidazole derivatives generally have good solubility in protic solvents. Simple imidazole derivatives, such as 1H-imidazole, 2-methyl-1H-imidazole, and 1,2-dimethylimidazole, have very high solubility in water. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Transformations of sugars in an ammoniacal medium was written by Parrod, Jacques. And the article was included in Annali di Chimica Applicata in 1933.Computed Properties of C4H5N3O This article mentions the following:

P. bubbled air through an aqueous solution containing levulose, NH₄OH and the hydroxide or sulphate of a metal (CaO, ZnO, FeSO₄, Fe₂(SO₄)₃ or MnSO₄) for 1 month at ordinary temperature; 4-methylimidazole was formed in all cases and 4-hydroxymethylimidazole in all cases except with CaO. In a repetition of the experiment without air the product was 4-methylimidazole in all cases, but in poor yields except with ZnO; in the single case with MnSO₄ there was also formed 2-hydroxymethyl-4-methylimidazole, C₅H₈ON₂, coarse needles, m. 129°; picrate, m. 82°. In a 2nd experiment with air a solution containing levulose, NH₄HCO₃ and Cu(OH)₂, oxalic acid and imidazoles were found among the reaction products. In a 3rd similar experiment with air, levulose was oxidized with methylene blue in the presence of NH₄OH; the products included 4-hydroxymethylimidazole, (d-arabino)-4-tetrahydroxybutylimidazole, and a new substance 4-imidazoleformamide, N:CH.NH.CH:CCONH₂.H₂O, large colorless efflorescent crystals, m. 214°; HCl salt, large prisms, m. 220°, picrate, yellow needles, m. 208°. In the experiment, the researchers used many compounds, for example, 1H-Imidazole-4-carboxamide (cas: 26832-08-6Computed Properties of C4H5N3O).

1H-Imidazole-4-carboxamide (cas: 26832-08-6) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Computed Properties of C4H5N3O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Carbon-13, nitrogen-14, nitrogen-15, and oxygen-17 NMR spectra of nitropyrroles and nitroimidazoles was written by Lippmaa, E.;Magi, M.;Novikov, S. S.;Khmelnitski, L. I.;Prihodko, A. S.;Lebedev, O. V.;Epishina, L. V.. And the article was included in Organic Magnetic Resonance in 1972.Recommanded Product: 3034-41-1 This article mentions the following:

C, N, and O NMR spectra of nitro derivatives of pyrrole and imidazole are investigated. The 13C chem. shifts of para-C atoms and the 17O chem. shifts of the nitro group correlate qual. with the electron ds. on these C and O atoms, which in turn depend upon the degree of conjugation of the nitro groups with the heterocyclic ring. Conjugation of several nitro groups with the benzene ring is not impaired by mutual interactions and the 13C shifts are additive. Additivity is much worse in pyrrole and imidazole derivatives Taken together with the diamagnetic nature of these deviations from additivity, this leads to a possible conclusion about the less pronounced conjugation of the nitro groups with the heterocyclic ring in heterocyclic dinitro derivatives In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Recommanded Product: 3034-41-1).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. The solubility of imidazoles in ethers is lower than that in alcohols and decreases with increasing chain length of the ethers . In contrast, the solubility of benzimidazoles in alcohols (C3–C6) is higher than in water and generally decreases with a Imidazole based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Recommanded Product: 3034-41-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Self-Assembly and Complexation of Cellulose/Ionic Liquid at High Cellulose Concentration: Anion Dependence was written by Endo, Takatsugu;Yoshida, Shota;Kimura, Yoshifumi. And the article was included in Crystal Growth & Design in 2020.COA of Formula: C7H13ClN2 This article mentions the following:

The authors studied the state of cellulose that was dissolved in ionic liquid (IL) consisting of 1-Me-3-propylimdiazolium cation ([C₃mim]⁺) paired with acetate ([OAc]^–), dimethylphospate ([DMP]^–), or chloride (Cl^–) anions using wide-angle x-ray scattering (WAXS), particularly focusing on the high cellulose concentration region (10-80 mol %). The anion species considerably altered the WAXS pattern of the cellulose/IL mixtures [C₃mim][OAc] deconstructed cellulose crystal structure up to the 40 mol % cellulose concentration Similar to the previously reported cellulose/1-Et-3-methylimidazolium acetate system ([C₂mim][OAc]), the mixtures of cellulose/[C₃mim][OAc] at 25-60 mol % induced a low angle peak, which corresponds to the self-assembly of the system. For [C₃mim][DMP] and [C₃mim]Cl mixtures, sharp Bragg peaks were observed, which demonstrated the formation of the complex crystal of cellulose/IL. The presence of moisture eventually deconstructed these crystal structures; while for [C₃mim]Cl, an intermediate complex crystal containing H₂O mols. emerged. This work contributes to understanding the cellulose state dissolved in IL at high concentrations and to the development of crystal engineering on this most abundant and recalcitrant biopolymer. Complex crystals formed when cellulose was simply mixed with a certain ionic liquid at high concentrations The complex crystals are sensitive to H₂O; they transformed into a different complex crystal or an amorphous state, depending on anion types used and H₂O concentration contained. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8COA of Formula: C7H13ClN2).

1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8) belongs to imidazole derivatives. The solubility of imidazoles in ethers is lower than that in alcohols and decreases with increasing chain length of the ethers . In contrast, the solubility of benzimidazoles in alcohols (C3–C6) is higher than in water and generally decreases with a Imidazole based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).COA of Formula: C7H13ClN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Hydrogenation sequence of acetophenone on commercial platinum catalyst AP-64 was written by Smirnova, N. A.;Adamyan, V. L.;Edigarova, E. I.. And the article was included in Azerbaidzhanskii Khimicheskii Zhurnal in 1987.Formula: C6H8N2O This article mentions the following:

Cyclohexyl Me carbinol formation from PhCOMe in the title reaction at 100-155° proceeded by parallel formation and hydrogenation of PhCHMeOH (I) and cyclohexyl Me ketone. Small amounts of I were also reduced to PhEt and then to ethylcyclohexane. In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Formula: C6H8N2O).

1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1) belongs to imidazole derivatives. The solubility of imidazoles in ethers is lower than that in alcohols and decreases with increasing chain length of the ethers . In contrast, the solubility of benzimidazoles in alcohols (C3–C6) is higher than in water and generally decreases with a This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Formula: C6H8N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Highly selective biocatalytic synthesis of monoacylglycerides in sponge-like ionic liquids was written by Lozano, Pedro;Gomez, Celia;Nieto, Susana;Sanchez-Gomez, Gregorio;Garcia-Verdugo, Eduardo;Luis, Santiago V.. And the article was included in Green Chemistry in 2017.Quality Control of 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide This article mentions the following:

The biocatalytic synthesis of monoacylglycerides (MAGs) was carried out by the direct esterification of fatty acids (i.e. capric, lauric, myristic, palmitic and oleic acids, resp.) with glycerol in different ionic liquids (ILs) based on cations with long alkyl side-chains (e.g. 1-hexadecyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide [C₁₆mim][NTf₂], 1-dodecyl-3-methylimidazolium tetrafluoroborate [C₁₂mim][BF₄], etc.). Although all ILs have been shown as suitable reaction media for Novozym 435-catalyzed esterification of glycerol with free fatty acids, a high selectivity of MAGs was only observed in the [C₁₂mim][BF₄] case (e.g. up to 100% selectivity and 100% yield for monolaurin). Furthermore, as these ILs are temperature switchable ionic liquid/solid phases that behave as sponge-like systems, a straightforward protocol for IL-free MAG recovery, based on iterative centrifugations at controlled temperature, has been developed. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Quality Control of 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide).

3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5) belongs to imidazole derivatives. 1H-imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole. Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.Quality Control of 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Oxone-DMSO Triggered Methylene Insertion and C(sp²)-C(sp³)-H-C(sp²) Bond Formation to Access Functional Bis-Heterocycles was written by Kour, Jaspreet;Venkateswarlu, Vunnam;Verma, Praveen K.;Hussain, Yaseen;Dubey, Gurudutt;Bharatam, Prasad V.;Sahoo, Subash C.;Sawant, Sanghapal D.. And the article was included in Journal of Organic Chemistry in 2020.Reference of 1632-83-3 This article mentions the following:

Metal-free insertion of a methylene group was achieved for the construction of a new C(sp²)-C(sp³)-H-C(sp²) bond in order to prepare novel bis-heterocyclic scaffolds. The complete mechanistic investigations included exptl. study and DFT calculations, and various sym. and unsym. bis-pyrazoles as well as other pyrazole-based bis-heterocyclic mols. were prepared in moderate to high yields. Further modification of the bridged methylene group in the unsym. pyrazoles generated a chiral center to extend the scope of this method. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Reference of 1632-83-3).

1-Methylbenzimidazole (cas: 1632-83-3) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole has been usedin the lysis, wash and elution buffer for the purification of histidine tagged Sonic Hedgehog(shh-N) protein, in elution buffer in stepwise gradient for the purification of histidine tagged aldo keto reductases using nickel affinity chromatography, as a component of homogenization buffer for the purification of phagosomal compartments from dendritic cells.Reference of 1632-83-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Preparation and Characterization of Titanium Tetrachloride-Based Ionic Liquids was written by Gao, Lixia;Wang, Lina;Qi, Tao;Chu, Jinglong;Qu, Jingkui. And the article was included in Journal of the Electrochemical Society in 2009.Application of 79917-89-8 This article mentions the following:

TiCl₄-based ionic liquids (ILs) were synthesized by mixing TiCl₄ with quaternary ammonium, pyridinium, and imidazolium chlorogenated salt, resp. The structure and composition of the ILs were studied with Fourier transform ICR mass spectrometry, IR, and Raman spectra. The primary anions of the TiCl₄-based ILs were Ti₂Cl₉^– and TiCl₆^2-, whose amounts were different by variation of the molar ratio of TiCl₄ to organic halogenated salt. The phys. properties such as the phase transition behavior, surface tension, d., viscosity, and conductivity of these ILs were also studied. Temperature-dependent viscosity and conductivity of the ILs followed the Vogel-Tammann-Fulcher equation, and the best-fit parameters had been estimated, together with the linear fitting parameters for the d. The conductivity and viscosity of the TiCl₄-based ILs were controlled by the ion mobility and the availability of voids with suitable dimensions. Hole theory could well explain the physicochem. properties of the TiCl₄-based ILs. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8Application of 79917-89-8).

1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8) belongs to imidazole derivatives. The solubility of imidazoles in ethers is lower than that in alcohols and decreases with increasing chain length of the ethers . In contrast, the solubility of benzimidazoles in alcohols (C3–C6) is higher than in water and generally decreases with a Imidazole has been usedin the lysis, wash and elution buffer for the purification of histidine tagged Sonic Hedgehog(shh-N) protein, in elution buffer in stepwise gradient for the purification of histidine tagged aldo keto reductases using nickel affinity chromatography, as a component of homogenization buffer for the purification of phagosomal compartments from dendritic cells.Application of 79917-89-8

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem