Imidazole CAS 288-32-4

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  • Appearance: White powder
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: Imidazole Supplement

Basic Info of Imidazole

What is Imidazole?

Imidazole is a five-membered aromatic heterocyclic substance including two meta-position nitrogen atoms in its molecular framework. The unshared electron pair of the 1-position nitrogen atom in the imidazole ring participates in the cyclic conjugation, as well as the electron density of the nitrogen atom decreases, making this nitrogen atomic. The hydrogen on the atom quickly leaves in the form of hydrogen ion. For that reason, imidazole is weakly acidic as well as can develop salts with strong bases.

The unshared electron set of the 3-position nitrogen atom in the imidazole ring does not participate in the conjugation, but inhabits the sp2 crossbreed orbital, which can approve protons and form salts with strong acids. Imidazole is slightly more basic than pyrazole and also pyridine. Tautomerism exists in the imidazole ring. The hydrogen on the 1-position nitrogen atom can be transferred to the 3-position nitrogen atom, so imidazole derivatives having the very same substituent at the 4-position and the 5-position, specifically, are tautomers. Imidazoles are acid secure and have antioxidant residential or commercial properties. By-products of imidazole exist commonly in nature. Such as histamine, histidine, benzimidazole and so forth.

Among the acyl substances of imidazoles are some intriguing reagents. For example 1-acetylimidazole is a steady acylating representative. Responds with pyrrole to produce 1-acetylpyrrole. Additionally, under typical circumstances, 1-acetylimidazole can create ketones and aldehydes by utilizing Grignard reagents as well as lowering representatives. N, N’-carbonyldiimidazole responds with the carboxyl team to provide the helpful reagent acylimidazole. The relationship between imidazoles as well as all-natural compounds is extremely close. As an example, after condensing with a pyrimidine ring, a purine derivative is gotten, which, along with being the base of nucleic acids such as 6-aminopurine and also guanine, likewise exists in uric acid, high levels of caffeine as well as theophylline in living organisms. The catalytic result of imidazole, such as sped up enzymatic hydrolysis, is under research. Allergic to the skin, and also its toxicity resembles that of diamines. Rat dental LD501880mg/kg.

Imidazole Uses

  1. Imidazoles are used as intermediates of fungicides such as imazalil and imazapyr, as well as intermediates of medicinal antifungal drugs econazole, ketoconazole and clotrimazole.
  2. Imidazoles are used as raw materials for organic synthesis and intermediates for the preparation of drugs and pesticides.
  3. Imidazoles are used as analytical reagents and are also used in organic synthesis.
  4. Pesticide intermediates, fungicides intermediates, triazole fungicides.

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Application of Imidazole

Imidazole is mainly used as a curing agent for epoxy resins. In Japan, consumption of imidazole is less than half. The dosage of imidazole compounds is 0.5% to 10% of epoxy resin, and can be used in antifungal, antifungal, hypoglycemic, artificial plasma, etc., and can also be used in the treatment of trichomoniasis and turkey blackhead. Imidazole is also one of the main raw materials for the production of imidazole antifungal drugs miconazole, econazole, clotrimazole and ketoconazole. Using imidazoles and 2, 4, ω-trichloroacetophenone as the main raw materials, the fruit fungicide enpirin can be prepared. 2, 4, ω-Trichloroacetophenone was added to anhydrous methanol, heated to reflux, and bromine was added. After the color of the solution disappeared gradually, it was cooled to 0 °C and stirred vigorously for 3 h. and vacuum distillation of methanol. The remaining liquid was taken into water and extracted with dichloromethane. After the extract is recovered with dichloromethane, dilute nitric acid is added to obtain the salt; recrystallized with water, and then treated with ammonia water to obtain 2′,4′-dichloro-2-imidazole acetophenone. It is then reduced to the corresponding alcohol with sodium borohydride, and then in the presence of sodium hydroxide and dimethylformamide, allyl chloride is used as the base to obtain enconazole (also known as enconazole). Then add dilute nitrate and water for recrystallization, and then treat 2,2′,4′-dichloro-2-methylimidazolyl acetophenone with ammonia water. Enconazole shares some commonalities with miconazole in structure and production methods.

Preparation of Imidazole

Using glyoxal as raw material, imidazole sulfate is obtained by reacting with formaldehyde and ammonium sulfate (or ammonia water) at 85 ~ 90 ℃, and then neutralized with calcium hydroxide to obtain crude imidazole. Filtration, water washing, the combination of filtrate and washing liquid, and the concentration and crystallization of vacuum evaporation can be completed. If ammonia water is directly used, there should be no sulfate treatment step and it can be prepared at one time. Whether it is ammonium sulfate or ammonia water, the yield is relatively low, about 45%.

Benzimidazole was synthesized from o-phenylenediamine and formic acid by cyclization, and then dicarbonyl imidazole was formed by oxidation in sulfuric acid solution; In the later stage, the crude product was obtained by decarboxylation at 100 ~ 150 ℃ under the oxidation of copper; And then recrystallized in benzene solution to obtain imidazole finished product.

Using d-tartaric acid as raw material, 2,3-dinitro-tartaric acid was obtained by nitration with nitric acid in sulfuric acid; And then reacted with formaldehyde and ammonia to obtain imidazole dicarboxylate; And finally decarboxylate to get it.


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