212485-91-1

Basic information

• Product Name: 4-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)PHENOL
• Synonyms: 2-(4-Hydroxyphenyl)-2-imidazoline
• CAS NO: 212485-91-1
• Molecular Formula: C₉H₁₀N₂O
• Molecular Weight: 162.19
• Product Categories: Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Imidazolines/Imidazolidines
• Mol File: 212485-91-1.mol

Chemical Properties

• Melting Point: 280 °C ( dec.)
• Boiling Point: 309.617°C at 760 mmHg
• Flash Point: 142.263°C
• Appearance: /
• Density: 1.217g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.593
• PKA: 7.84±0.30(Predicted)
• CAS DataBase Reference: 4-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)PHENOL(212485-91-1)
• EPA Substance Registry System: 4-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)PHENOL(212485-91-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 212485-91-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
DHPI is used as a building block for the synthesis of various pharmaceuticals and organic molecules, leveraging its unique chemical structure to create new compounds with potential therapeutic properties.
Used in Cancer Research:
In the field of cancer research, DHPI is used as a potential anti-cancer agent. Its specific molecular structure allows it to be studied for its effects on different types of cancer, with the aim of developing targeted therapies.
Used in Alzheimer's Disease Research:
DHPI is also being investigated for its potential as a treatment for Alzheimer's disease. Its role in this context is to be explored for possible neuroprotective effects or other mechanisms that could contribute to managing or treating the disease.
Used in Medicinal Chemistry:
In medicinal chemistry, DHPI is employed for its versatility in compound development. Its unique structure and properties make it a valuable component in designing new drugs and therapies for various medical conditions.
Used in Drug Development:
DHPI's potential applications in drug development are vast, as it can be incorporated into the creation of new pharmaceuticals. Its presence in a compound may enhance efficacy, improve pharmacokinetics, or provide other benefits that are crucial in the development of effective treatments.

InChI:InChI=1/C9H10N2O/c12-8-3-1-7(2-4-8)9-10-5-6-11-9/h1-4,10-11H,5-6H2

Upstream product

• 874-90-8 4-methoxybenzonitrile 
• 123-08-0 4-hydroxy-benzaldehyde 
• 107-15-3 ethylenediamine 
• 767-00-0 4-cyanophenol 
• 90437-28-8 N-(2-aminoethyl)-4-hydroxybenzamide 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 69731-90-4 methyl 4-hydroxybenzimino ester HCl 
• 57943-60-9 4-hydroxybenzimidic acid methyl ester hydrochloride 
• 6302-84-7 2-(4-methoxyphenyl)-4,5-dihydro-1H-imidazole 

Downstream Products

• 15548-89-7 2-(4-hydroxyphenyl)-1H-imidazole 
• 100-01-6 4-nitro-aniline 
• 137208-88-9 1-methyl-2-(4-hydroxyphenyl)-1H-imidazoline 

Relevant articles and documents

4-(Cyclic amidino)phenols-preparation and use in a diamidine synthesis

The Pinner synthesis was applied to the preparation of 4-(cyclic amidino)phenols in high yields from readily available 4-hydroxybenzimidic acid methyl ester hydrochloride and diaminoalkanes. An alternative attempt was made to convert 4-(hydroxy)thiobenzamide to 4-(1,4,5,6-terahydro-5- hydroxy-2-pyrimidinyl)phenol. A procedure for the preparation of 3,6-bis(4- hydroxyphenyl)-1,2,4,5-tetrazine is reported here. The syntheses of 2,4- bis[4-(4,5-dihydro-1H-imidazol-2-yl)phenoxy]pyrimidine and 2-chloro-4-[4- (4,5-dihydro-1H-imidazol-2-yl)-phenoxy]pyrimidine exemplify the use of the title synthetic intermediates.

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Disclosed herein are small molecule Vascular Adhesion Protein- 1 (VAP-1) modulator compositions, pharmaceutical compositions, the use and preparation thereof.

Synthesis of tetrazoles, triazoles, and imidazolines catalyzed by magnetic silica spheres grafted acid

The magnetically separable catalysts are used in the synthesis of N-containing heterocycles, including tetrazoles, triazoles, and imidazolines. The magnetic silica sphere grafted sulfonic acid (MSS-SO3H) is suitable for the synthesis of 1,2,3-triazole via the cycloaddition of nitroalkene with NaN3, whereas the zinc-modified silica sphere catalyst (MSS-SO3Zn) is more suitable for the synthesis of tetrazoles. The MSS-SO3Zn catalyst also works well for the synthesis of 2-substituted imidazoline via the condensation of nitriles with ethylenediamine. Both of the MSS-SO3H and MSS-SO3Zn catalysts can be recovered easily by a magnet, and they can be reused without further tedious activation.

New quinoline-arylamidine hybrids: Synthesis, DNA/RNA binding and antitumor activity

Four series of new hybrid molecules with 7-chloroquinoline and arylamidine moieties joined through the rigid -O- (groups I (2a-g) and II (5a-g)) or flexible -NH-CH2-CH2-O- (groups III (8a-g) and IV (10a-g)) linker were synthesized, and their DNA/RNA binding properties and cytotoxic activity were tested, against several human cancer lines. The compounds and their interaction with DNA and RNA were studied by UV–Vis and CD spectroscopy. The obtained results showed that the binding affinity of the investigated compounds increases proportionally with the increase of the length and number of groups able to form hydrogen bonds with ds-polynucleotides. Improvement of binding was additionally achieved by reduction of the structural rigidity of the investigated compounds, new hybrid compounds preferentially bind to ctDNA. For most of them the DNA/RNA grooves are dominant binding sites, except for the compounds from group II for which intercalation in polyA-polyU was the dominant binding mode. The antiproliferative effects were tested by the MTT test on normal (MDCK1), carcinoma (HeLa and CaCo2) and leukemia cell lines (Raji and K462). The GI50 values for all investigated compounds ranged from 5 to more than 100 × 10?6 mol dm?3. Carcinoma cells were more resistant to the investigated compounds than leukemia cells. The most effective compounds against leukemia cell lines were from group IV (10a-g), with GI50 values ranging from of 5 and 35 × 10?6 mol dm?3. The cell cycle arrest was investigated by flow cytometry and the obtained results indicate that the selected compounds, 2d, 2e, 8a, 10d, 10e, and 10f, induce changes in the cell cycle of treated cells, but the cycle phase distribution varies between them. A significant decrease in the number of cells in S phase (p 0.001) was observed in all treated cells, but only 10d and 10f induce cell cycle arrest at G0/G1 phase, dominantly.

Fe3O4@SiO2@polyionene/Br3- core-shell-shell magnetic nanoparticles: A novel catalyst for the synthesis of imidazole derivatives under solvent-free conditions

New Fe3O4@SiO2@polyionene/Br3- core-shell-shell magnetite nanoparticles were prepared using a co-precipitation method and were used in the syntheses of imidazole derivatives under solvent-free conditions. The polyionene was easily prepared by reacting DABCO and 1,4-dibromo butane in DMF/methanol. It was then added to the previously formed layers and magnetic core-shell nanoparticles (P-MNPs) were functionalized. All the resultant nanoparticles were characterized by transmission electron microscopy (TEM), scanning electron microscopy (SEM), infrared spectroscopy (FTIR), X-ray diffraction (XRD), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and vibrating sample magnetometry (VSM). The catalyst was readily recovered by simple magnetic decantation and can be recycled several times with no significant loss of catalytic activity.

Reactivity of hydroxy and amino derivatives of 2-phenyl-1H-imidazoline and 2-phenyl-1H-imidazole toward isocyanates: Synthesis of appropriate carbamates and ureas

Reactivity of 2-(4-hydroxyphenyl)-1H-imidazoline and 2-(4-hydroxyphenyl)- 1H-imidazole toward substituted phenyl isocyanates was studied. When mentioned imidazoline was treated with 2.5 equiv of substituted phenyl isocyanate, three N,O-dicarboxamides were

Efficient and one-pot catalytic synthesis of 2-imidazolines and bis-imidazolines with p-toluenesulfonic acid under solvent free conditions

A practical, efficient, and inexpensive method for the synthesis of 2-imidazoline from the reaction of nitriles with ethylenediamine or 1,2-propanediamine using p-toluenesulfonic acid or pyridinium p-toluenesulfonate under reflux conditions is reported. This catalyst can be successfully applied for the chemoselective conversion of dicyanobenzenes to corresponding mono- and bis-imidazolines. The applications of these catalysts are feasible because of easy preparation, easy handling, stability, inexpensive, good activity, and eco-friendly.

Efficient catalytic synthesis of 2-imidazolines and bis-imidazolines with silica supported tungstosilicic acid

A rapid and efficient preparation of 2-imidazolines and bis-imidazolines by the reaction of ethylenediamine or 1,2-propanediamine with nitriles in the presence of catalytic amounts of tungstosilicic acid supported on SiO 2 under reflux condition, is reported. The advantages of this procedure are moderate reaction times, good to high yields and the ability to carry out the large scale reactions. ARKAT USA, Inc.

Mild and efficient one-pot synthesis of 2-imidazolines from nitriles using sodium hydrosulfide as catalyst

A simple and efficient method has been developed for the synthesis of 2-imidazolines through a one-pot reaction of various nitriles with ethylenediamine in the presence of sodium hydrosulfide as catalyst in high yield. Copyright Taylor & Francis Group, LLC.

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