Imidazole Powder CAS 288-32-4

Imidazole powder, molecular formula C3H4N2, white to yellow crystalline powder. It is an organic compound, a kind of diazole, and a five membered aromatic heterocyclic compound with two meta nitrogen atoms in its molecular structure. The unconsumed electron pair of the 1-position nitrogen atom in the imidazole ring participates in the ring conjugation, and the electron density of the nitrogen atom decreases, making the hydrogen on this nitrogen atom easy to leave in the form of hydrogen ions.

Imidazole is acidic and alkaline, and can form salts with strong bases. The chemical properties of imidazole can be summarized as the synthesis of pyridine and pyrrole. These two structural units just play an important role in the catalysis of lipoid hydrolysis by histidine as an acyl transfer agent in the enzyme. Imidazole derivatives exist in biological organisms and are more important than imidazole itself in scientific research and industrial production, such as DNA, hemoglobin, etc.

Imidazole powder, a five membered aromatic heterocyclic compound containing two meta nitrogen atoms, has demonstrated extraordinary application value in the fields of medicine, agriculture, industry, and scientific research due to its unique electronic structure and reactivity.

Antifungal therapy

 

Mechanism of action:
Inhibition of ergosterol synthesis: Imidazole drugs (such as clotrimazole and ketoconazole) block ergosterol synthesis on fungal cell membranes by inhibiting lanosterol 14 α - demethylase.
Clinical application:
Skin ringworm disease: External application of miconazole nitrate ointment for the treatment of tinea pedis, with a cure rate of 85% (4-week course).
Deep fungal infection: Fluconazole is used for candidemia, with oral bioavailability>90%.

Thyroid disease treatment

 

Antithyroid drugs:
Methimazole (MMI): inhibits thyroid peroxidase, reduces thyroid hormone synthesis, and takes 2-3 weeks to take effect.
Advantages of Function:
Embryo safety: MMI is recommended as a priority in early pregnancy, with a lower risk of teratogenicity than propylthiouracil.

Development of anti-tumor drugs

 

Imidazole derivatives:
Gambogic acid: a multi target inhibitor, IC50 is 0.8 μ M for breast cancer MCF-7 cells.
Combination therapy:
Imidazole platinum complex: After coordination with imidazole, cisplatin reduces nephrotoxicity by 40% and increases anti-tumor activity by 2 times.

Central nervous system drugs

 

Sedative hypnotic drugs:
Etomidate: The imidazole ring structure enhances its lipophilicity, rapidly crosses the blood-brain barrier, and has an anesthesia induction time of less than 30 seconds.
antiepileptic:
Zonisamide: an imidazole tetrahydrofuran structure that inhibits voltage-gated sodium channels, resulting in a 75% control rate for status epilepticus.

Fungicide

 

Benzimidazole class:
Duojunling: prevents and treats wheat Fusarium head blight, with a field efficacy of 82%. Its mechanism of action is to interfere with microtubule protein polymerization.
Advantages and Characteristics:
Intrinsic activity: Conducted upwards through root absorption, protecting newly formed tissues.
Resistance management: alternate use with triazole fungicides to delay the development of resistance.

Insecticides

 

Neonicotinoids:
Imidacloprid: acts on insect nicotinic acetylcholine receptors and has a 48 hour mortality rate of>95% against aphids.
Mode of action:
Internal absorption conduction: Distributed to various parts of the plant 24 hours after application, with a shelf life of 30 days.

Plant growth regulation

 

Root development:
Imidazoacetic acid (IA): A concentration of 0.1 ppm promotes a 25% elongation of Arabidopsis main roots and a 30% increase in the number of lateral roots.
Enhancement of resilience:
Imidazole powder glycerophosphate (IGP): improves wheat drought resistance and increases leaf relative water content by 18%.

Post harvest preservation

 

Prochloraz:
Prevention and control of citrus penicillium disease: soaking treatment after harvest can inhibit the expansion of disease spots by 90% and extend the storage period by 4 weeks.
Mechanism of action:
Respiratory inhibition: reduces the release of ethylene from fruits and delays the ripening process.

 

(1) Epoxy resin curing agent
Performance improvement:
Mechanical properties: Adding 2% imidazole increases the bending strength of epoxy resin by 35% and the glass transition temperature (Tg) by 15 ℃.
Technological advantages:
Low temperature curing: It can be completely cured at 80 ℃/2 hours and is suitable for packaging thermal sensitive components.
(2) Metal surface treatment
Copper rust inhibitor:
Benzotriazole (BTA) substitution: Imidazole derivatives have a corrosion inhibition efficiency of 92% and a cost reduction of 40%.
Aluminum anodizing:
Uniformity of film layer: Adding 0.5% imidazole reduces the porosity of the oxide film by 25% and increases the corrosion resistance by three times.

 

(3) Chemical synthesis intermediates
Drug synthesis:
Carbonyl diimidazole (CDI): a peptide coupling reagent that promotes amino acid condensation with a yield of>95%.
Dye industry:
Disperse dyes: Imidazole structure enhances the affinity of dyes for polyester fibers, with a color fastness of 4-5 levels.
(4) Other industrial applications
Glass industry:
Clarifier: Eliminate bubbles in the glass, improve transparency, and consume 0.2 kg of imidazole per ton of glass.
Rubber vulcanization:
Accelerator: Imidazole derivatives shorten vulcanization time by 30% and increase crosslinking density.

 

(1) Materials Science
Ionic liquids:
1-Ethyl-3-methylimidazolium tetrafluoroborate: melting point 12 ℃, electrochemical window>4V, suitable for lithium-ion battery electrolyte.
Metal organic frameworks (MOFs):
ZIF-8： The imidazole ligand was used to construct a zeolite structure with a hydrogen adsorption capacity of 2.6 wt% (77 K/1 atm).
(2) Catalytic field
Asymmetric catalysis:
Chiral imidazoline ligand: In iridium catalyzed asymmetric hydrogenation, ee value>99%.
Photocatalysis:
Imidazole modified TiO ₂: visible light response, methyl orange degradation rate of 85% (2 hours).

1. It is obtained by cyclization and neutralization of glyoxal. Put glyoxal, formaldehyde and ammonium sulfate into the reaction pot, stir and heat them to 85-88 ℃, and keep them warm for 4h. Cool to 50-60 ℃, and use lime water until the pH is above 10. Heat to 85-90 ℃, discharge ammonia for more than 1h, cool slightly, filter, wash the filter cake with hot water, concentrate the filtrate under reduced pressure until it is evaporated without water, continue to distill under reduced pressure until all low boiling substances are evaporated, and collect 105-160 ℃ (0.133-0.267kPa) distillate to obtain imidazole. The yield is about 45%.

2. Another preparation method is to cyclize o-phenylenediamine and formic acid to generate benzimidazole, then open the ring to 4,5-dihydroxyimidazole through hydrogen peroxide reaction, and finally decarboxylate to obtain imidazole. 4,5-Dihydroxyimidazole can also be obtained by nitration and cyclization of D-tartaric acid. The process of decarboxylation of 4,5-dihydroxyimidazole to prepare imidazole is as follows: mix 4,5-dihydroxyimidazole with copper oxide, heat to 100-280 ℃, release a large amount of carbon dioxide gas, collect distillate to obtain crude product, and recrystallize with benzene to obtain finished product with a yield of 76%.

3. Industrial glyoxal synthesis method: put glyoxal, formaldehyde and ammonium sulfate into the reactor, stir and heat them to 85~88 ℃, and keep them warm for 4h. Then cool it to 50~60 ℃, use lime water to reach pH above 10, then heat it to 85~90 ℃, and discharge ammonia for more than 1h. After slightly cooling, filter, wash the filter cake with hot water, add the filtrate to the distillation unit, first reduce the pressure and concentrate until no water is evaporated, then continue to reduce the pressure and distill until all the low boiling substances are evaporated, and then collect 105~160 ℃/133.3~266.7Pa fraction to obtain imidazole. The yield is about 45%. Each ton of product consumes 4172kg glyoxal, 2344kg formaldehyde (37%), 3826kg ammonium sulfate (99%) and 2571kg lime. The reaction formula is as follows:

Due to the unsatisfactory yield and product quality, some improved methods were reported in the literature, such as the method of isopropyl ether extraction, the synthesis method of using urotropine instead of formaldehyde, the synthesis method of using ammonia instead of ammonium sulfate, and the synthesis method of using ammonium oxalate instead of ammonium sulfate. If ammonium oxalate is used instead of ammonium sulfate, the yield can be increased to 65%.

4. Cyclization of o-phenylenediamine and formic acid: o-phenylenediamine and formic acid are cyclized to form benzimidazole, which is then opened to 4,5-dicarboxylic imidazole by hydrogen peroxide reaction, and finally decarboxylated to prepare imidazole.

5. Bromoacetaldehyde method: add vinyl acetate and bromine, then treat with ethanol to generate bromoacetaldehyde, and then react with hydrogen bromide and ethanol to generate acetal. Acetal generates cyclic acetal under the action of ethylene glycol and concentrated hydrochloric acid, and reacts with acetal with excess formamide under the condition of continuous introduction of ammonia to generate imidazole with a yield of 50%.

Imidazole powder is more prone to electrophilic aromatic substitution than other 1,3-diazoles, and the reaction mainly takes place on C-4 and C-5. This is because there is a particularly unstable limit formula when electrophilic reagents attack C-2, and the generated intermediates distribute positive charges on nitrogen atoms. For example, the reaction of imidazole with fuming nitric acid/concentrated sulfuric acid can quickly generate 4 (5) - nitroimidazole with high yield; However, the nitration of 4,5-dimethylimidazole still could not take place under severe conditions.

The electron cloud density on imidazole N-3 is large, so the alkylation reaction generally takes place on this nitrogen atom first. Through tautomerism, the monoalkylated product can generate a nitrogen atom similar to pyridine, so it can further react to generate the dialkylation product imidazolium salt.

The acylation reaction of imidazole generally occurs on N-3, but because the acyl group is an electron withdrawing group, the reaction can be controlled in the single acylation stage, and the product is N-acyl imidazole.

The active hydrogen of imidazole can decompose Grignard reagent to produce N-magnesium salt of imidazole, and then obtain C-2 substituted imidazole after isomerization. The latter can be treated with iodomethane to produce 1,2-dimethylimidazole.

Imidazole can be added to the dienophile, first forming a 3-onium salt zwitterion, and then nucleophilic addition with another dienophile to generate a C-2 cyclized product. For example, 1-methyl-2-ethylimidazole reacts with two molecules of dimethyl succinate to obtain 8 α- Ethyl-1-methyl-1,8 α- Tetramethyl dihydroimidazolo [1,2-a] pyridine-5,6,7,8-tetracarboxylate.

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