Imidazole Basic informationProduct Name:ImidazoleSynonyms:Imidazole [for Fluorimetric Analysis];Glyoxaline, lminazole;IMIDAZOLE extrapure AR;IMIDAZOLE pure;IMIDAZOLEANALYTICAL GRADE;IMIDAZOLERESEARCH GRADE;Imidazole,1,3-Diaza-2,4-cyclopentadiene, Glyoxaline;Ondansetron impurity E (Ph Eur)CAS:288-32-4MF:C3H4N2MW:68.08EINECS:206-019-2Product Categories:Pharmaceutical intermediates;Buffer;Highly Purified Reagents;Other Categories;Zone Refined Products;Biochemistry;Reagents for Oligosaccharide Synthesis;Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;Intermediate for Propafenone hydrochloride.;ACS Grade Buffers;ACS Grade;Biological Buffers;Buffers A to Z;Building Blocks;C3 to C8;Chemical Synthesis;Essential Chemicals;Heterocyclic Building Blocks;Imidazoles;Inorganic Salts;Research Essentials;Solutions and Reagents;2-8°C;288-32-4;API;3;bc0001Mol File:288-32-4.mol Imidazole Chemical PropertiesMelting point 88-91 °C(lit.)Boiling point 256 °C(lit.)density 1.01 g/mL at 20 °Cvapor pressure <1 mm Hg ( 20 °C)refractive index 1.4801Fp 293 °Fstorage temp. Store below +30°C.solubility H2O: 0.1 M at 20 °C, clear, colorlessform crystallinepka6.953(at 25℃)Specific Gravity1.03color whiteOdorAmine likePH Range9.5 – 11PH9.5-11.0 (25℃, 50mg/mL in H2O)Water Solubility 633 g/L (20 ºC)Sensitive Hygroscopicλmaxλ: 260 nm Amax: 0.10λ: 280 nm Amax: 0.10Merck 14,4912BRN 103853Stability:Stable. Incompatible with acids, strong oxidizing agents. Protect from moisture.InChIKeyRAXXELZNTBOGNW-UHFFFAOYSA-NLogP-0.02 at 25℃CAS DataBase Reference288-32-4(CAS DataBase Reference)NIST Chemistry Reference1H-Imidazole(288-32-4)EPA Substance Registry SystemImidazole (288-32-4)Safety InformationHazard Codes C,Xi,TRisk Statements 36/38-63-34-22-20/21/22-61Safety Statements 26-36/37/39-45-22-36-27-53RIDADR UN 2923 8/PG 3WGK Germany 1RTECS NI3325000Autoignition Temperature480 °CTSCA YesHazardClass 8PackingGroup IIIHS Code 29332990Hazardous Substances Data288-32-4(Hazardous Substances Data)ToxicityLD50 in mice (mg/kg): 610 i.p.; 1880 orally (Nishie)MSDS InformationProviderLanguageACROSEnglishSigmaAldrichEnglishALFAEnglishImidazole Usage And SynthesisChemical PropertiesImidazole is a moderately strong base (pKb= 7.0), and a weak acid (pKa= 14.9). Imidazoles substituted with electron-withdrawing groups are stronger acids than imidazole itself; e.g., 4(5)-nitroimidazole has a pKa of 9.3. Imidazole is stable at 400°C, possesses considerable aromatic character, and undergoes the usual electrophilic aromatic substitution reactions. Nitration and sulfonation require, however, far more drastic conditions than the corresponding reactions with benzene. Other substitution reactions of imidazole include halogenation, hydroxymethylation, coupling with aromatic diazonium salts, and carboxylation.HistoryImidazole[288-32-4] was first synthesized in 1858 by Debus from ammonia and glyoxal; it was originally named glyoxalin. The name imidazole was introduced by Hantzsch. Industrial production of imidazole began in the 1950s; a wide range of derivatives is now available in industrial quantities.UsesImidazole is used as a buffer in the range of pH 6.2-7.8. It is also an histamine antagonist. It acts as a chelator and forms complexes with various divalent cations. It is used as a corrosion inhibitor on certain transition metals such as copper. Its derivatives, like polybenzimidazole (PBI), act as fire retardants. It finds application in photography and electronics. Imidazole salts are used as ionic liquids and precursors to stable carbenes. Imidazole derivatives like ketoconazole, miconazole and clotrimazole are involved in the treatment of various systemic fungal infections. It is a part of the theophylline molecule, present in tea leaves and coffee beans, which stimulates the central nervous system.DefinitionChEBI: 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. It is an important pharmacophore in drug discovery. Imidazole is used as a Karl Fischer reagent in analytical chemistry and a reagent in synthetic organic chemistry.ApplicationImidazole is a versatile heterocycle used in the preparation of various biologically active compounds such as the amino acid histidine and is present in many antifungal medication. It is also used ext ensively as a corrosion inhibitor on transition metals such as copper.It is used in organic synthesis and as an antiirradiationagent. Imidazole has been used: in 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 cell.PreparationImidazole is formed by reacting glyoxal with formaldehyde in the presence of ammonium acetate in acetic acid. The driving energy is microwave radiation. More generally, this reaction is used to produce substituted imidazoles.  Although there had been discoveries of various derivatives of imidazole in 1840, it was first reported in 1858. The synthesis process of imidazole follows the reaction between formaldehyde in ammonia and glyoxal. This process gives low yield of imidazole but it is still used to form imidazole with C-substitution (Wolkenberg et al., 2004).General DescriptionImidazole 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.Health HazardIt is less toxic relative to pyrrole and otherfive-membered heterocyclic compounds ofnitrogen. Intraperitoneal administration ofimidazole caused somnolence, muscle contractions,and convulsions in mice. Theoral LD50 value in mice is in the range900 mg/kg.Fire HazardNoncombustible solid.Biochem/physiol ActionsImidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division. It also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes. 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).Purification MethodsCrystallise imidazole from *benzene, CCl4, CH2Cl2, EtOH, pet ether, acetone/pet ether and distilled de-ionized water. Dry it at 40o under vacuum over P2O5. Distil it at low pressure. It is also purified by sublimation or by zone melting. [Snyder et al. Org Synth Coll Vol III 471 1955, Bredereck et al. Chem Ber 97 827 1964, Caswell & Spiro J Am Chem Soc 108 6470 1986.] 15N-imidazole crystallises from *benzene [Scholes et al. J Am Chem Soc 108 1660 1986]. [Beilstein 23 II 34, 23 III/IV 564, 23/4 V 191.]Imidazole Preparation Products And Raw materialsRaw materialsHydrochloric acid–>Potassium hydroxide–>Ammonium hydroxide–>Hydrogen peroxide–>Ammonium chloride–>Formaldehyde–>o-Phenylenediamine–>Glyoxal–>Cupric oxide–>Benzimidazole–>4,5-Imidazoledicarboxylic acidPreparation Products5-(AMINOMETHYL)-1-METHYLPYRROLIDIN-2-ONE–>(S)-4-BOC-MORPHOLINE-3-CARBOXYLIC ACID–>1-Boc-3-(Amino)azetidine–>beta-Methyl vinyl phosphate (MAP)–>6-FLUORO-1H-PYRAZOLO[3,4-B]PYRIDINE-3-CARBONITRILE–>1-Methylimidazole–>5-Bromoindazole–>6-FLUORO-1H-PYRAZOLO[3,4-B]PYRIDINE-3-CARBOXYLIC ACID–>2-CYANOPYRIDINE-4-CARBOXALDEHYDE–>Imazalil–>4-(HYDROXYMETHYL)PICOLINITRILE–>2-(1H-IMIDAZOL-1-YL)BENZOIC ACID–>Clotrimazole–>Econazole–>Miconazole nitrate–>Sisthsne–>Ketoconazole–>1-[4-(BROMOMETHYL)PHENYL]-1H-PYRAZOLE–>Imidazole-2-carboxaldehyde–>2,6-Dihydroxypurine–>4-Chloroimidazole–>4-(IMIDAZOL-1-YL)PHENOL–>2-Bromo-4-nitroimidazole–>Oxiconazole nitrate–>TRIFLUMIZOLE–>1-BENZYL-2-IMIDAZOLECARBOXYLIC ACID–>1-Phenylimidazole–>4-(1H-Imidazol-1-yl)benzaldehyde–>2-Imidazol-1-ylethanamine–>N-(3-Aminopropyl)-imidazole–>4-(1H-IMIDAZOL-1-YL)BENZOIC ACID–>Climbazole–>Orazamide–>1-[(4-Methylphenyl)sulfonyl]-1H-imidazole–>imidazol-2-ylamine sulphate–>1-(1-2-HYDROXYPHENYL)ETHENYL)-1H-IMIDAZOLE–>chloroalcohol type homogeneous strongly basic anion exchange membrane–>1-METHYL-5-NITROIMIDAZOLE–>4-Nitroimidazole–>Detergent,industrial |
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