31659-42-4

Basic information

• Product Name: 4,5-dihydro-2-(3-nitrophenyl)-1H-imidazole
• Synonyms: 4,5-dihydro-2-(3-nitrophenyl)-1H-imidazole;2-(3-nitrophenyl)-4,5-dihydro-1H-imidazole
• CAS NO: 31659-42-4
• Molecular Formula: C₉H₉N₃O₂
• Molecular Weight: 191.18666
• EINECS: 250-754-1
• Product Categories: Heterocyclic Compounds;Imidaxoles
• Mol File: 31659-42-4.mol

Chemical Properties

• Melting Point: 156-157 °C
• Boiling Point: 334.7 °C at 760 mmHg
• Flash Point: 156.2 °C
• Appearance: /
• Density: 1.41 g/cm³
• Vapor Pressure: 0.000126mmHg at 25°C
• Refractive Index: 1.673
• PKA: 9.32±0.40(Predicted)
• CAS DataBase Reference: 4,5-dihydro-2-(3-nitrophenyl)-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-dihydro-2-(3-nitrophenyl)-1H-imidazole(31659-42-4)
• EPA Substance Registry System: 4,5-dihydro-2-(3-nitrophenyl)-1H-imidazole(31659-42-4)

Safety Data

• Hazardous Substances Data: 31659-42-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4,5-Dihydro-2-(3-nitrophenyl)-1H-imidazole is used as an intermediate in the synthesis of Imidazolide Dipropionate, a compound with potential pharmaceutical applications. Its role in the synthesis process is crucial for the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4,5-dihydro-2-(3-nitrophenyl)-1H-imidazole serves as a versatile intermediate for the preparation of various imidazole-based compounds. Its unique structure allows for further functionalization and modification, enabling the creation of a wide range of chemical products with diverse applications.

InChI:InChI=1/C9H9N3O2/c13-12(14)8-3-1-2-7(6-8)9-10-4-5-11-9/h1-3,6H,4-5H2,(H,10,11)

Upstream product

• 618-95-1 methyl 3-nitrobenzoate 
• 107-15-3 ethylenediamine 
• 619-24-9 3-nitrobenzonitrile 
• 99-61-6 3-nitro-benzaldehyde 
• 936-49-2 2-phenyl-2-imidazoline 
• 619-25-0 3-Nitrobenzyl alcohol 

Downstream Products

• 94086-79-0 2-(3-aminophenyl)imidazoline 
• 27885-92-3 imidocarb 
• 55750-06-6 imidocarb dipropionate 
• 5318-76-3 imidocarb hydrochloride 
• 53104-89-5 2-(3-aminophenyl)-4,5-dihydro-1H-imidazol hydrochloride 
• 121-92-6 3-nitrobenzoic acid 

Relevant articles and documents

Preparation method of imidocarb dipropionate and intermediate thereof

The invention discloses a preparation method of imidocarb dipropionate and an intermediate thereof and belongs to the technical field of chemical pharmacy. According to the method, m-nitrobenzonitrilereacts with ethylenediamine with sodium sulfide taken as a catalyst; palladium on carbon-ammonium formate reduction is performed; a product and urea are subjected to condensation reaction, so that imidazole phenylurea dihydrochloride can be obtained; dissociated imidazole phenylurea reacts with propionic acid, so that the imidazole phenylurea dipropionate can be obtained. The method has the advantages o reduced wastes, cheap and easily available raw materials, simple operation, high product yield, simple process operation and high safety, and is suitable for industrial production.

Preparation method of 2-(3-amino phenyl) imidazoline hydrochloride and imidocarb

The invention relates to the field of chemical engineering and discloses a preparation method of 2-(3-amino phenyl) imidazoline hydrochloride and imidocarb. The preparation method comprises the following steps of: inputting 2-(3-nitryl phenyl) imidazoline, a catalyst and an alcohol-water mixed solution into a reaction kettle, stirring the mixture and raising the temperature to 50-65 DEG C, keeping the temperature and stirring the mixture for 10-20 min to obtain a mixed solution M; dropwise adding formic acid into the solution M, and keeping the temperature to react for 1.5-2.5h to obtain a mixed solution N; cooling the solution N to 40 DEG C below and filtering the solution, and evaporating alcohol to obtain a 2-(3-amino phenyl) imidazoline aqueous solution; dropwise adding hydrochloric acid into the 2-(3-amino phenyl) imidazoline aqueous solution to be neutral; and performing crystallization, suction filtration, pressure reduction and drying to obtain a target product 2-(3-amino phenyl) imidazoline hydrochloride. Compared with catalytic hydrogenation in the prior art, by taking formic acid as a hydrogen donor for transfer hydrogenation, the product purity and yield are of no obvious differences but no safety risks are available, and the preparation method is free of special demand, easy to operate and convenient for production and application.

A process for the preparation of imidazole

The invention relates to a preparation method of imidocarb. The preparation method comprises the steps of dissolving methyl-m-nitrobenzoate into a solvent, enabling methyl-m-nitrobenzoate and ethylenediamine to be subjected to cyclization reaction at the temperature of 55-65 DEG C for 3-6h under the action of a catalyst, and separating to prepare m-nitroimidazoline; dissolving m-nitroimidazoline into a water solution of methanol, adding zinc powder under an acidic condition, after the addition is ended, carrying out reduction reaction for 1-2h while stirring at normal temperature, and separating and purifying to prepare m-aminoimidazoline; dissolving m-aminoimidazoline into a water solution of tetrahydrofuran, regulating the pH value to 7-10, adding triphosgene, reacting at the temperature of 10-40 DEG C for 2-6h, filtering and drying to obtain imidocarb. Methyl-m-nitrobenzoate is used as a starting raw material, and zinc powder is used as a reducing agent, so that the preparation method is mild in reaction condition, convenient in operation and relatively low in cost.

A Highly Efficient Single-Chain Metal-Organic Nanoparticle Catalyst for Alkyne-Azide "click" Reactions in Water and in Cells

We show that copper-containing metal-organic nanoparticles (MONPs) are readily synthesized via Cu(II)-mediated intramolecular cross-linking of aspartate-containing polyolefins in water. In situ reduction with sodium ascorbate yields Cu(I)-containing MONPs that serve as highly efficient supramolecular catalysts for alkyne-azide "click chemistry" reactions, yielding the desired 1,4-adducts at low parts per million catalyst levels. The nanoparticles have low toxicity and low metal loadings, making them convenient, green catalysts for alkyne-azide "click" reactions in water. The Cu-MONPs enter cells and perform efficient, biocompatible click chemistry, thus acting as intracellular nanoscale molecular synthesizers.

Antibacterial drug leads: DNA and enzyme multitargeting

We report the results of an investigation of the activity of a series of amidine and bisamidine compounds against Staphylococcus aureus and Escherichia coli. The most active compounds bound to an AT-rich DNA dodecamer (CGCGAATTCGCG)2 and using DSC were found to increase the melting transition by up to 24 °C. Several compounds also inhibited undecaprenyl diphosphate synthase (UPPS) with IC50 values of 100-500 nM, and we found good correlations (R2 = 0.89, S. aureus; R2 = 0.79, E. coli) between experimental and predicted cell growth inhibition by using DNA δTm and UPPS IC50 experimental results together with one computed descriptor. We also solved the structures of three bisamidines binding to DNA as well as three UPPS structures. Overall, the results are of general interest in the context of the development of resistance-resistant antibiotics that involve multitargeting.

Efficient synthesis of 2-imidazolines in the presence of molecular iodine under ultrasound irradiation

An efficient one-pot synthesis process for preparing 2-imidazolines from aldehydes and ethylenediamine using molecular iodine and potassium carbonate in absolute ethanol at 25-30°C under ultrasound irradiation is described. The synthetic strategy has the following advantages: mild conditions and low costs requirements, readily available catalyst, short reaction times, simplicity of operation, and good-to-excellent yields.

A facile and efficient synthesis of 2-imidazolines from aldehydes using hydrogen peroxide and substoichiometric sodium iodide

The reaction of aldehydes with ethylenediamine for the preparation of 2-imidazolines has been studied using hydrogen peroxide as an oxidant in the presence of sodium iodide and anhydrous magnesium sulfate. A mild, green, and efficient method is established to carry out this reaction in high yield. Georg Thieme Verlag Stuttgart · New York.

Cyclopalladated complexes of 2-(m-nitrophenyl)imidazolines: Synthesis, characterization and catalytic activity in the Suzuki reaction under mild conditions

Three cyclopalladated complexes of 2-(m-nitro-phenyl)imidazolines have been easily prepared and characterized by spectroscopic analysis. The structure of one of the complexes has been determined by single-crystal X-ray analysis. The complexes are effective catalysts for the Suzuki reaction of aryl bromides with phenylboronic acid in aqueous solution at room temperature under air. Springer Science+Business Media B.V. 2010.

Ultrasound promoted synthesis of 2-imidazolines in water: A greener approach toward monoamine oxidase inhibitors

A series of sixteen 2-substituted-2-imidazolines (where the substituent R = Ph, Me-4-Ph; MeO-4-Ph; (MeO)2-3,4-Ph; (MeO)3-3,4,5-Ph; Ph-4-O-C(O)-Ph; Cl-4-Ph; Cl-2-Ph; Cl2-2,4-Ph; NO2-4-Ph; NO2-3-Ph; Naphth-2-yl; Fur-2-yl; Benzofur-2-yl; Pyridin-2-yl; Quinolin-2-yl) has been synthesized from the reaction of the substituted-aldehydes and ethylenediamine by ultrasound irradiation with NBS in an aqueous medium in high yields (80-99%). The 2-imidazoline ability to inhibit the activity of the A and B isoforms of monoamine oxidase (MAO) was investigated and some of them showed potent and selective MAO inhibitory activity especially for the MAO-B isoform and could become promising candidates for future development.

Mono-nitration of aromatic compounds via their nitric acid salts

Aromatic compounds bearing a basic nitrogen atom can be converted to the corresponding nitric acid salts. Mono-nitration of the compounds can be carried out by adding a dichloromethane solution of the salts to sulfuric acid, or by adding acetyl chloride (or trifluoroacetic anhydride) to a dichloromethane solution of the salts. This protocol provides, among other benefits, the most convenient and reliable way for the prevention of over-/under-nitration and is especially suitable for scale-up.