Chemistry Heterocyclic Building Blocks Imidazoles

Imidazoles

Imidazole (ImH) has the chemical formula C3N2H4 and exists as a white or colorless solid which is capable of dissolving in water and forming a mildly alkaline solution. As an aromatic heterocycle, it belongs to the diazole class of organic compounds and has meta-substituted nitrogen atoms that are non-adjacent to each other.

With its planar 5-membered ring structure, imidazole exhibits two equivalent tautomeric forms due to the ability of hydrogen to bind to either of its nitrogen atoms. Imidazole is a compound of high polarity, as demonstrated by its electric dipole moment of 3.67 D, and it is readily soluble in water.

Imidazole exhibits amphoterism, meaning that it can function as both an acid and a base. When it acts as an acid, the nitrogen-bound proton of imidazole is acidic with a pKa of 14.5, which makes it less acidic than carboxylic acids, phenols, and imides, but slightly more acidic than alcohols.

Imidazole is an aromatic five-membered molecule that comprises of two nitrogen atoms within the ring structure. One of the nitrogen atoms exhibits pyrrole-type behavior, while the other closely resembles a pyridine-type nitrogen.

Many important biological compounds contain imidazole, with the most common example being the amino acid histidine, which features an imidazole side-chain. Histidine is a constituent of numerous proteins and enzymes, where it binds metal cofactors, as observed in hemoglobin.

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By Key Group+−

aminoimidazole-carboxylate benzyl-imidazole benzyl-methyl-imidazole biimidazole bromo-imidazole bromo-imidazopyridine bromo-methyl-imidazole bromoimidazo bromoimidazole carboxylate chloro-imidazopyridine chloroimidazo dibromoimidazo dichloroimidazo dihydroimidazo dimethyl-imidazol dimethylimidazo dimethylimidazolium dioxaborolane-imidazole ethyl-imidazole fluoroimidazo hydroxy-imidazopyridine imidazol-amine imidazol-hydrochloride imidazol-ium imidazol-methanamine imidazol-methanol imidazol-pyridine imidazole imidazole-carboxylate imidazole-carboxylic acid imidazolyl-ethanol imidazolyl-nitrile imidazolyl-pyrimidine imidazopyrazine imidazopyridazine imidazopyridin-amine imidazopyridin-one imidazopyridine imidazopyridine-carbonitrile imidazopyridine-carboxylate imidazopyridine-carboxylic-acid imidazopyrimidine imidazoquinoline imidazothiazole iodoimidazo iodomethyl-imidazole isopropyl-imidazole methoxyimidazo methyl-imidazopyridine methyl-nitro-imidazole methylimidazo methylimidazole methylimidazolium nitro-imidazole-carboxylate nitroimidazole phenylimidazo phenylimidazole piperidin-imidazolyl pyrroloimidazole tetrahydroimidazo thienoimidazol trifluoromethyl-imidazo trifluoromethyl-imidazole trifluoromethyl-imidazopyridine

By Parent Nucleus+−

Aliphatic Heterocycles Aromatic Heterocycles Dioxolanes Indazoles Other Aliphatic Heterocycles Other Aromatic Heterocycles Piperazines Piperidines Pyrazines Pyrazoles Pyridines Pyrimidines Pyrrolidines Spiroes Tetrahydropyrans Thiophenes Thiophenols Triazines Triazoles

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Alcohols Aldehydes Aliphatic Chain Hydrocarbons Aliphatic Cyclic Hydrocarbons Alkenyls Alkynyls Amides Amines Aryls Benzyl bromides Benzyl Chlorides Bromides Carboxylic Acids Chiral Building Blocks Chlorides Esters Ethers Fluorinated Building Blocks Hydrazines Iodides Ketones Nitriles Nitroes Organoboron Oximes Phenols Phosphoruses Sulfamides Sulfides Sulfonates Sulfones Sulfonic Acids Sulfonyl Chlorides Sulfoxides Thioureas Trifluoromethyls Ureas

Framework+−

1,1'-diphenyl-4,4',5,5'-tetrahydro-1H,1'H-2,2'-biimidazole 1,2-dimethyl-1H-imidazole 1,3-diphenyl-1H-imidazol-3-ium 1,3-diphenyl-4,5-dihydro-1H-imidazol-3-ium 1-(imidazo[1,2-a]pyridin-3-yl)ethan-1-one 1-(phenylsulfonyl)-1H-imidazole 1-benzyl-1H-imidazole 1-decyl-3-methyl-1H-imidazol-3-ium 1-ethyl-1H-imidazole 1-isopropyl-1H-imidazole 1-phenyl-1H-imidazole-4-carboxylic acid 1-trityl-1H-imidazole 1H-imidazo[4,5-b]pyridine 1H-imidazo[4,5-c]pyridine 1H-imidazol-2-amine 1H-imidazole-2-carboxylic acid 1H-imidazole-4-carbonitrile 1H-imidazole-4-carboxylic acid 2-(pyridin-2-yl)-1H-benzo[d]imidazole 2-bromo-1H-imidazole 2-bromoimidazo[1,2-a]pyridine 2-ethyl-1H-imidazole 2-methyl-1-phenyl-1H-imidazole 2-methylimidazo[1,2-a]pyridine 2-phenyl-1H-benzo[d]imidazole 2-phenyl-1H-imidazole 2-phenylimidazo[1,2-a]pyridine 2-propyl-1H-imidazole 3-bromoimidazo[1,2-a]pyrazine 3-bromoimidazo[1,2-a]pyridine 3-bromoimidazo[1,2-a]pyrimidine 3-iodoimidazo[1,2-a]pyridine 3-methylimidazo[1,2-a]pyridine 4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine 4-(1H-imidazol-1-yl)benzaldehyde 4-bromo-1-phenyl-1H-imidazole 4-methyl-1-phenyl-1H-imidazole 4-methyl-1H-imidazole 4-phenyl-1H-imidazole 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine 5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine 5-benzyl-1H-imidazole 5-bromoimidazo[1,2-a]pyridine 5-chloro-1H-imidazole 5-fluoro-1H-benzo[d]imidazole 5-iodo-1H-imidazole 5-methylimidazo[1,2-a]pyridine 5-phenyl-1H-imidazole 6,7-dihydro-5H-pyrrolo[1,2-a]imidazole 6-bromoimidazo[1,2-a]pyrazine 6-bromoimidazo[1,2-a]pyridine 6-bromoimidazo[1,2-a]pyrimidine 6-chloroimidazo[1,2-a]pyridine 6-chloroimidazo[1,2-b]pyridazine 7-methylimidazo[1,2-a]pyridine 8-bromoimidazo[1,2-a]pyrazine 8-bromoimidazo[1,2-a]pyridine 8-chloroimidazo[1,2-a]pyrazine 8-chloroimidazo[1,2-a]pyridine 8-fluoroimidazo[1,2-a]pyridine 8-methylimidazo[1,2-a]pyridine ethyl 1H-imidazole-2-carboxylate ethyl 2-(imidazo[1,2-a]pyridin-3-yl)acetate ethyl imidazo[1,2-a]pyridine-2-carboxylate ethyl imidazo[1,2-a]pyridine-3-carboxylate imidazo[1,2-a]pyridin-3-amine imidazo[1,2-a]pyridin-8-amine imidazo[1,2-a]pyridin-8-ol imidazo[1,2-a]pyridine-2-carbaldehyde imidazo[1,2-a]pyridine-2-carboxylic acid imidazo[1,2-a]pyridine-3-carbaldehyde imidazo[1,2-a]pyridine-3-carboxylic acid imidazo[1,2-a]pyridine-7-carboxylic acid imidazo[1,2-a]pyridine-8-carboxylic acid imidazo[1,2-a]pyrimidine-3-carboxylic acid imidazo[1,2-c]pyrimidine imidazo[1,5-a]pyrazine imidazo[2,1-b]thiazole methyl 1H-imidazole-2-carboxylate methyl 1H-imidazole-5-carboxylate methyl imidazo[1,2-a]pyridine-8-carboxylate tert-butyl 1H-imidazole-1-carboxylate

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    5-(1H-Imidazol-1-yl)isophthalic acid

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    2-Phenyl-1H-imidazole

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    4-(1H-Imidazol-1-yl)benzaldehyde

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    1-(Pyridin-4-yl)-1H-imidazole-4-carboxylic acid

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    4-(4,5-Diphenyl-1H-imidazol-2-yl)benzoic acid

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    4,5-Dicyanoimidazole

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    3,6-Di(1H-imidazol-1-yl)pyridazine

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    2-(4-Aminophenyl)-1H-benzimidazol-5-amine

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    4-(1H-imidazol-1-yl)benzonitrile

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    5-[4-(1-Imidazolyl)phenyl]-2H-tetrazole

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    2-(2-Bromophenyl)-1H-benzo[d]imidazole

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    1,3,5-Tri(1H-imidazol-1-yl)benzene

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    8-Bromo-6-chloroimidazo[1,2-a]pyridine-3-carbaldehyde

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    1-(4-Bromophenyl)imidazole

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