Category: 3034-41-1

Proton nuclear magnetic resonance spectra of aryl and mono- and disubstituted N-methylazoles was written by Butler, Richard Noel. And the article was included in Canadian Journal of Chemistry in 1973.Recommanded Product: 3034-41-1 This article mentions the following:

Proton NMR spectra of substituted azoles, e.g., methylpyrrole, imidazoles, pyrazoles, etc., are compared. The influence of the azole ring on the chem. shifts of phenyl protons is discussed. A correlation between N-Me chem. shifts and the structural characteristics of the N-Me group in mono- and disubstituted azoles is noted. 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. Imidazole is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. 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

NMR Chemical Shift and Methylation of 4-Nitroimidazole: Experiment and Theory* was written by Backler, Frederick;Sani, Marc Antoine;Separovic, Frances;Vasilyev, Vladislav;Wang, Feng. And the article was included in Australian Journal of Chemistry in 2021.Safety of 1-Methyl-4-nitroimidazole This article mentions the following:

Nitroimidazoles and derivatives are a class of active pharmaceutical ingredients (APIs) first introduced sixty years ago. As anti-infection agents, the structure-activity relationships of nitroimidazole compounds have been particularly difficult to study due to their low reduction potentials and unique electronic structures. In this study, we combine dynamic nuclear polarization (DNP)-enhanced solid-state (100K), solid-state (298K), and ¹H-¹³C heteronuclear single quantum coherence (HSQC) solution-state NMR techniques (303K) with d. functional theory (DFT) to study the 1H, 13C, and 15N chem. shifts of 4-nitroimidazole (4-NI) and 1-methyl-4-nitroimidazole (CH₃-4NI). The 4-NI chem. shifts were observed at 119.4, 136.4, and 144.7ppm for 13C, and at 181.5, 237.4, and 363.0ppm for 15N. The measurements revealed that methylation (deprotonation) of the amino nitrogen N(1) of 4-NI had less effect (螖未=-4.8ppm) on the N(1) chem. shift but was compensated by shielding of the N(3) (螖未=11.6ppm) in CH₃-4NI. The calculated chem. shifts using DFT for 4-NI and CH₃-4NI agreed well with the exptl. values (within 2%) for the imidazole carbons. However, larger discrepancies (up to 13%) were observed between the calculated and measured 15N NMR chem. shifts for the imidazole nitrogen atoms of both mols., which indicate that effects such as imidazole ring resonant structures and mol. dynamics may also contribute to the nitrogen chem. environment. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Safety of 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) 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 also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Safety of 1-Methyl-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Prediction of the Formation and Stabilities of Energetic Salts and Ionic Liquids Based on ab Initio Electronic Structure Calculations was written by Gutowski, Keith E.;Holbrey, John D.;Rogers, Robin D.;Dixon, David A.. And the article was included in Journal of Physical Chemistry B in 2005.Recommanded Product: 1-Methyl-4-nitroimidazole This article mentions the following:

A computational approach to predict the thermodn. for forming a variety of imidazolium-based salts and ionic liquids from typical starting materials is described. The gas-phase proton and Me cation acidities of several protonating and methylating agents, as well as the proton and Me cation affinities of many important methyl-, nitro-, and cyano-substituted imidazoles, have been calculated reliably by using the computationally feasible DFT (B3LYP) and MP2 (extrapolated to the complete basis set limit) methods. These accurately calculated proton and Me cation affinities of neutrals and anions are used in conjunction with an empirical approach based on mol. volumes to estimate the lattice enthalpies and entropies of ionic liquids, organic solids, and organic liquids These quantities were used to construct a thermodn. cycle for salt formation to reliably predict the ability to synthesize a variety of salts including ones with potentially high energetic densities. An adjustment of the gas phase thermodn. cycle to account for solid- and liquid-phase chemistries provides the best overall assessment of salt formation and stability. This has been applied to imidazoles (the cation to be formed) with alkyl, nitro, and cyano substituents. The proton and Me cation donors studied were as follows: HCl, HBr, HI, (HO)₂SO₂, HSO₃CF₃ (TfOH), and HSO₃(C₆H₄)CH₃ (TsOH); CH₃Cl, CH₃Br, CH₃I, (CH₃O)₂SO₂, CH₃SO₃CF₃ (TfOCH₃), and CH₃SO₃(C₆H₄)CH₃ (TsOCH₃). As substitution of the cation with electron-withdrawing groups increases, the triflate reagents appear to be the best overall choice as protonating and methylating agents. Even stronger alkylating agents should be considered to enhance the chances of synthetic success. When using the enthalpies of reaction for the gas-phase reactants to form a salt, a cutoff value of -13 kcal mol^-1 or lower (more neg.) should be used as the min. value for predicting whether a salt can be synthesized. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Recommanded Product: 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) 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.Recommanded Product: 1-Methyl-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Nucleophilic Aromatic Substitution Reactions Described by the Local Electron Attachment Energy was written by Stenlid, Joakim H.;Brinck, Tore. And the article was included in Journal of Organic Chemistry in 2017.Recommanded Product: 3034-41-1 This article mentions the following:

A local multiorbital electrophilicity descriptor, the local electron attachment energy [E(r)], is used to study the nucleophilic aromatic substitution reactions of S_NAr and VNS (vicarious nucleophilic substitution). E(r) considers all virtual orbitals below the free electron limit and is determined on the mol. isodensity contour of 0.004 at units. Good (R² = 0.83) to excellent (R² = 0.98) correlations are found between descriptor values and exptl. reactivity data for six series of electron deficient arenes. These include homo- and heteroarenes, rings of five to six atoms, and a variety of fluorine, bromine, and hydride leaving groups. The solvent, temperature, and nucleophile are in addition varied across the series. The surface E(r) [E_S(r)] provides reactivity predictions better than those of transition-state calculations for a concerted S_NAr reaction with a bromine nucleofuge, gives correlations substantially stronger than those of LUMO energies, and is overall more reliable than the mol. electrostatic potential. Using E_S(r), one can identify the various electrophilic sites within a mol. and correctly predict isomeric distributions. Since the calculations of E_S(r) are computationally inexpensive, the descriptor offers fast but accurate reactivity predictions for the important nucleophilic aromatic substitution class of reactions. Applications in, e.g., drug discovery, synthesis, and toxicol. studies are envisaged. 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. Imidazole is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. 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.Recommanded Product: 3034-41-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reactions of organic anions. Part 143. Vicarious nucleophilic substitution of hydrogen in imidazole derivatives was written by Makosza, Mieczyslaw;Kwast, Ewa. And the article was included in Bulletin of the Polish Academy of Sciences, Chemistry in 1987.Quality Control of 1-Methyl-4-nitroimidazole This article mentions the following:

Nitroderivatives of imidazole react with carbanions containing leaving groups at the carbanion center yielding products of vicarious nucleophilic substitution of H at positions activated by the nitro group. Thus, nitroimidazole I reacted with PhSO₂CH₂Cl in the presence of KOH in Me₂SO to give derivative II. Some aspects of the orientation pattern of substitution are discussed. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Quality Control of 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.n increase of the alkyl chain length of the alcohols. Quality Control of 1-Methyl-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis of heteroxanthine from a derivative of imidazole was written by Sarasin, J.;Wegmann, E.. And the article was included in Helvetica Chimica Acta in 1924.Application In Synthesis of 1-Methyl-4-nitroimidazole This article mentions the following:

S. and W. describe a new synthesis of 7-methylxanthine from an imidazole derivative, by closing the pyrimidine ring, an operation which has not been previously effected. 1-Methyl-4-nitro-5-chloroimidazole (I) is obtained in theoretical yield from 1-methyl-5-chloroimidazole (b. 200掳) (II) by dissolving in dilute HNO₃ to form the nitrate, treating the latter with cold concentrated H₂SO₄, heating the mixture on the water bath for 2 hrs., and pouring the product on ice; it m. 147-8掳, and is insoluble in acids and dilute alkalies. The isomeric 1-methyl-5-nitro-4-chloroimidazole (III), obtained by the same method from 1-methyl-4-chloroimidazole; m. 77-8掳. I and III are reduced at 0掳 by Sn and HCl to the corresponding methylchloroaminoimidazoles which were not obtained in the pure state. I heated for several hrs. on the H₂O bath in EtOH with 2 mols. KCN and 0.1 mol. KI yields 85% 1-methyl-4-nitro-5-cyanoimidazole (IV), m. 141-2掳, insoluble in acids and dilute alkalies. 1-Methyl-4-nitroimidazole-5-carboxamide (V), obtained in 90% yield when IV is heated for 2 hrs. on the H₂O bath with 8 times its weight of concentrated H₂SO₄ and the product is poured on ice, m. 257-8掳 (decomposes), insoluble in acids and alkalies, saponified with great difficulty; a small amount of the acid (VI) is obtained by prolonged action of concentrated HCl. VI m. 160掳 with evolution of CO₂ and formation of 1-methyl-4-nitroimidazole (VII), m. 133-40掳, which is also obtained by heating V in a sealed tube at 120掳 with HCl. Reduction of VII by Sn and HCl at 0掳 and hydrolysis of the product by heating under pressure with HCl, gives NH₄Cl and sarcosine-HCl, m. 168-9掳; this reaction establishes the constitution of II and VII. V is reduced at 0掳 by Sn and HCl to the corresponding amine, 1-methyl-4-aminoimidazole-5-carboxamide (VIII), m. 184-5掳, decomposed when heated with water or dilute alkalies with evolution of NH₃; HCl salt, m. 214-5掳. 7-Methylxanthine (heteroxanthine) obtained in 38% yield by heating 0.4 g. of VIII for 8 hrs. in a sealed tube at 160-70掳 with an equal weight of CO(OEt)₂, m. 380掳 (browning and evolution of gas). A mixture of the substance with heteroxanthine prepared from theobromine melts at the same temperature The murexide reaction is given with KClO₃ and HCl. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Application In Synthesis of 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) 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 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.Application In Synthesis of 1-Methyl-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis of heteroxanthine from a derivative of imidazole was written by Sarasin, J.;Wegmann, E.. And the article was included in Helvetica Chimica Acta in 1924.Application In Synthesis of 1-Methyl-4-nitroimidazole This article mentions the following:

S. and W. describe a new synthesis of 7-methylxanthine from an imidazole derivative, by closing the pyrimidine ring, an operation which has not been previously effected. 1-Methyl-4-nitro-5-chloroimidazole (I) is obtained in theoretical yield from 1-methyl-5-chloroimidazole (b. 200°) (II) by dissolving in dilute HNO₃ to form the nitrate, treating the latter with cold concentrated H₂SO₄, heating the mixture on the water bath for 2 hrs., and pouring the product on ice; it m. 147-8°, and is insoluble in acids and dilute alkalies. The isomeric 1-methyl-5-nitro-4-chloroimidazole (III), obtained by the same method from 1-methyl-4-chloroimidazole; m. 77-8°. I and III are reduced at 0° by Sn and HCl to the corresponding methylchloroaminoimidazoles which were not obtained in the pure state. I heated for several hrs. on the H₂O bath in EtOH with 2 mols. KCN and 0.1 mol. KI yields 85% 1-methyl-4-nitro-5-cyanoimidazole (IV), m. 141-2°, insoluble in acids and dilute alkalies. 1-Methyl-4-nitroimidazole-5-carboxamide (V), obtained in 90% yield when IV is heated for 2 hrs. on the H₂O bath with 8 times its weight of concentrated H₂SO₄ and the product is poured on ice, m. 257-8° (decomposes), insoluble in acids and alkalies, saponified with great difficulty; a small amount of the acid (VI) is obtained by prolonged action of concentrated HCl. VI m. 160° with evolution of CO₂ and formation of 1-methyl-4-nitroimidazole (VII), m. 133-40°, which is also obtained by heating V in a sealed tube at 120° with HCl. Reduction of VII by Sn and HCl at 0° and hydrolysis of the product by heating under pressure with HCl, gives NH₄Cl and sarcosine-HCl, m. 168-9°; this reaction establishes the constitution of II and VII. V is reduced at 0° by Sn and HCl to the corresponding amine, 1-methyl-4-aminoimidazole-5-carboxamide (VIII), m. 184-5°, decomposed when heated with water or dilute alkalies with evolution of NH₃; HCl salt, m. 214-5°. 7-Methylxanthine (heteroxanthine) obtained in 38% yield by heating 0.4 g. of VIII for 8 hrs. in a sealed tube at 160-70° with an equal weight of CO(OEt)₂, m. 380° (browning and evolution of gas). A mixture of the substance with heteroxanthine prepared from theobromine melts at the same temperature The murexide reaction is given with KClO₃ and HCl. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Application In Synthesis of 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) 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 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.Application In Synthesis of 1-Methyl-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reactions of organic anions. Part 143. Vicarious nucleophilic substitution of hydrogen in imidazole derivatives was written by Makosza, Mieczyslaw;Kwast, Ewa. And the article was included in Bulletin of the Polish Academy of Sciences, Chemistry in 1987.Quality Control of 1-Methyl-4-nitroimidazole This article mentions the following:

Nitroderivatives of imidazole react with carbanions containing leaving groups at the carbanion center yielding products of vicarious nucleophilic substitution of H at positions activated by the nitro group. Thus, nitroimidazole I reacted with PhSO₂CH₂Cl in the presence of KOH in Me₂SO to give derivative II. Some aspects of the orientation pattern of substitution are discussed. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Quality Control of 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.n increase of the alkyl chain length of the alcohols. Quality Control of 1-Methyl-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Nucleophilic Aromatic Substitution Reactions Described by the Local Electron Attachment Energy was written by Stenlid, Joakim H.;Brinck, Tore. And the article was included in Journal of Organic Chemistry in 2017.Recommanded Product: 3034-41-1 This article mentions the following:

A local multiorbital electrophilicity descriptor, the local electron attachment energy [E(r)], is used to study the nucleophilic aromatic substitution reactions of S_NAr and VNS (vicarious nucleophilic substitution). E(r) considers all virtual orbitals below the free electron limit and is determined on the mol. isodensity contour of 0.004 at units. Good (R² = 0.83) to excellent (R² = 0.98) correlations are found between descriptor values and exptl. reactivity data for six series of electron deficient arenes. These include homo- and heteroarenes, rings of five to six atoms, and a variety of fluorine, bromine, and hydride leaving groups. The solvent, temperature, and nucleophile are in addition varied across the series. The surface E(r) [E_S(r)] provides reactivity predictions better than those of transition-state calculations for a concerted S_NAr reaction with a bromine nucleofuge, gives correlations substantially stronger than those of LUMO energies, and is overall more reliable than the mol. electrostatic potential. Using E_S(r), one can identify the various electrophilic sites within a mol. and correctly predict isomeric distributions. Since the calculations of E_S(r) are computationally inexpensive, the descriptor offers fast but accurate reactivity predictions for the important nucleophilic aromatic substitution class of reactions. Applications in, e.g., drug discovery, synthesis, and toxicol. studies are envisaged. 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. Imidazole is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. 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.Recommanded Product: 3034-41-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Prediction of the Formation and Stabilities of Energetic Salts and Ionic Liquids Based on ab Initio Electronic Structure Calculations was written by Gutowski, Keith E.;Holbrey, John D.;Rogers, Robin D.;Dixon, David A.. And the article was included in Journal of Physical Chemistry B in 2005.Recommanded Product: 1-Methyl-4-nitroimidazole This article mentions the following:

A computational approach to predict the thermodn. for forming a variety of imidazolium-based salts and ionic liquids from typical starting materials is described. The gas-phase proton and Me cation acidities of several protonating and methylating agents, as well as the proton and Me cation affinities of many important methyl-, nitro-, and cyano-substituted imidazoles, have been calculated reliably by using the computationally feasible DFT (B3LYP) and MP2 (extrapolated to the complete basis set limit) methods. These accurately calculated proton and Me cation affinities of neutrals and anions are used in conjunction with an empirical approach based on mol. volumes to estimate the lattice enthalpies and entropies of ionic liquids, organic solids, and organic liquids These quantities were used to construct a thermodn. cycle for salt formation to reliably predict the ability to synthesize a variety of salts including ones with potentially high energetic densities. An adjustment of the gas phase thermodn. cycle to account for solid- and liquid-phase chemistries provides the best overall assessment of salt formation and stability. This has been applied to imidazoles (the cation to be formed) with alkyl, nitro, and cyano substituents. The proton and Me cation donors studied were as follows: HCl, HBr, HI, (HO)₂SO₂, HSO₃CF₃ (TfOH), and HSO₃(C₆H₄)CH₃ (TsOH); CH₃Cl, CH₃Br, CH₃I, (CH₃O)₂SO₂, CH₃SO₃CF₃ (TfOCH₃), and CH₃SO₃(C₆H₄)CH₃ (TsOCH₃). As substitution of the cation with electron-withdrawing groups increases, the triflate reagents appear to be the best overall choice as protonating and methylating agents. Even stronger alkylating agents should be considered to enhance the chances of synthetic success. When using the enthalpies of reaction for the gas-phase reactants to form a salt, a cutoff value of -13 kcal mol^-1 or lower (more neg.) should be used as the min. value for predicting whether a salt can be synthesized. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Recommanded Product: 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) 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.Recommanded Product: 1-Methyl-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem