1565-39-5

Usage

Uses

Used in Pharmaceutical Industry:
2-(4,5-Dihydro-1H-Imidazol-2-yl)Phenol is used as a reactant for the synthesis of α1-Adrenoceptor agonists, which are important in the development of medications targeting the adrenergic system. These agonists can be used to treat various conditions, such as hypotension and urinary incontinence.
Used in Chemical Synthesis:
2-(4,5-Dihydro-1H-Imidazol-2-yl)Phenol serves as a reactant for the synthesis of polymer-anchored oxovanadium(IV) complexes. These complexes have potential applications in catalysis and other chemical processes due to their unique properties.
Used in Organic Chemistry:
2-(4 5-DIHYDRO-1H-IMIDAZOL-2-YL)PHENOL is used as a reactant in oxidative aromatization reactions of imidazolines. These reactions are important for the synthesis of various organic compounds with potential applications in pharmaceuticals, agrochemicals, and other industries.
Used in Inorganic Chemistry:
2-(4,5-Dihydro-1H-Imidazol-2-yl)Phenol is also used in the study of intramolecular nitrogen-phosphorous interactions of phosphate esters. Understanding these interactions can provide insights into the structure and reactivity of various inorganic compounds, which can be useful in the development of new materials and catalysts.

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

Upstream product

• 6780-13-8 1,2-ethanediamine monohydrate 
• 51618-01-0 ethyl 2-hydroxybenzimidate hydrochloride 
• 611-20-1 salicylonitrile 
• 107-15-3 ethylenediamine 
• 65-45-2 salicylamide 
• 69-72-7 salicylic acid 
• 65739-83-5 2,3-dihydro-5H-imidazo<1,2-c><1,3->benzoxazin-5-one 
• 79576-70-8 2-(2-Hydroxyphenyl)-1,3-benzoxazin-4-thion 
• 63963-47-3 6,6'-(1,2,4-Dithiazolidin-3,5-yliden)-bis-2,4-cyclohexadien-1-on 
• 119-36-8 methyl salicylate 
• 88220-37-5 2-<(chloroethyl)aminocarbonyloxy>benzonitrile 
• 1218-69-5 2-(2-hydroxyphenyl)-4H-benzo[e][1,3]oxazin-4-one 

Downstream Products

• 52755-90-5 2’-(2-hydroxyphenyl)imidazole 
• 78584-02-8 2-(o-Butoxyphenyl)-Δ²-imidazolin 
• 912338-37-5 2-(2-isobutoxyphenyl)-1H-imidazoline 
• 912338-39-7 2-(2'-benzyloxyphenyl)-4,5-dihydroimidazole 
• 78584-01-7 2-(2-ethoxyphenyl)-1H-imidazoline 
• 912338-35-3 2-(2-propoxyphenyl)-1H-imidazoline 
• 912338-38-6 2-(2-sec-butoxyphenyl)-1H-imidazoline 
• 78584-00-6 2-(2-methoxyphenyl)-4,5-dihydro-1H-imidazole 
• 52091-35-7 2-(2-methoxyphenyl)-1H-imidazole 
• 912338-42-2 2-(2-isopropoxyphenyl)-1H-imidazole 

Relevant academic research and scientific papers

Four-electron oxidative dehydrogenation induced by proton-coupled electron transfer in ruthenium(III) complex with 2-(1,4,5,6-tetrahydropyrimidin-2-yl) phenolate

New ruthenium(II or III) complexes with general formula [Ru(O-N)(bpy) 2]n+ (O-N = unsymmetrical bidentate phenolate ligand; bpy = 2,2'-bipyridine) were synthesized, and their crystal structures and electrochemical properties were cha

Identification of Adenosine Deaminase Inhibitors by Metal-binding Pharmacophore Screening

Adenosine deaminase (ADA) is a human mononuclear Zn2+ metalloenzyme that converts adenosine to inosine. ADA is a validated drug target for cancer, but there has been little recent work on the development of new therapeutics against this enzyme. The lack of new advancements can be partially attributed to an absence of suitable assays for high-throughput screening (HTS) against ADA. To facilitate more rapid drug discovery efforts for this target, an in vitro assay was developed that utilizes the enzymatic conversion of a visibly emitting adenosine analogue to the corresponding fluorescent inosine analogue by ADA, which can be monitored via fluorescence intensity changes. Utilizing this assay, a library of ～350 small molecules containing metal-binding pharmacophores (MBPs) was screened in an HTS format to identify new inhibitor scaffolds against ADA. This approach yielded a new metal-binding scaffold with a Ki value of 26±1 μM.

Structurally diverse arene-fused ten-membered lactams accessed via hydrolytic imidazoline ring expansion

Imidazoline-fused [1,4]oxazepines (prepared in two simple steps from methyl 2-hydroxyaroates, ethylene diamine and bis-electrophilic aromatics) undergo a facile, good-yielding hydrolytic imidazoline ring expansion (HIRE) upon N-alkylation and treatment with aqueous K2CO3. The resulting arene-fused ten-membered lactams significantly add to the contemporary arsenal of small-molecule scaffolds where medium-sized ring systems are severely underrepresented.

Atom-economical construction of tetracyclic [1,4]oxazepines involving intramolecular arylation of a 2-imidazoline moiety

Novel [1,4]oxazepines containing a fused imidazoline moiety were synthesized from 2-hydroxyphenyl imidazolines and bis-electrophilic aromatic substrates in a reaction involving sequential nucleophilic aromatic substitution steps and a Smiles rearrangement. A notable step was the remarkably facile, metal-free intramolecular N-arylation of the imidazoline moiety with a fluoro-, nitro- or chloroaromatic or heteroaromatic ring. The approach presented in this Letter not only details access to a new, medicinally relevant tetracyclic [1,4]oxazepine core but also extends the scope of imidazoline arylation chemistry.

Effect of ortho-substituents on the stereochemistry of 2-(o-substituted phenyl)-1H-imidazoline-palladium complexes

Palladium complexes composed of [Pd(Ln)2Cl2] (n = 1, 2, 3, 4, 6), [L5a]2[PdCl4] and [Pd(L5b)2], where L1 = 4,5-dihydro-2-phenyl-1H-imidazole (=2-phenyl-1H-imidazoline), L2 = 2-(o-fluorophenyl)-1H-imidazoline, L3 = 2-(o-methylphenyl)-1H-imidazoline, L4 = 2-(o-tert-butylphenyl)-1H-imidazoline, L5a = 2-(o-hydroxyphenyl)-1H- imidazolinium, L5b = 2-(1H-imidazolin-2-yl)phenolate, and L6 = 2-(o-methylphenyl)-1H-imidazole, were synthesized. Molecular structures of the isolated palladium complexes were characterized by single crystal X-ray diffraction analysis. The effect of ortho-substituents on the phenyl ring on trans-chlorine geometry was noted for complexes [Pd(L1)2Cl 2] 1a and 1b, [Pd(L2)2Cl2] 2 and [Pd(L6) 2Cl2] 6, whereas cis-chlorine geometry was observed for [Pd(L3)2Cl2] 3 and [Pd(L4)2Cl2] 4. PdCl2 reacts with 2-(o-hydroxyphenyl)-1H-imidazoline in DMF to give [L5a]+ and [L5b]- so that [L5a]2[PdCl 4] 5a and [Pd(L5b)2] 5b were obtained. In complex 5b, as an N,O-bidentate ligand, two ligands L5b coordinated with the central Pd(II) ion in the trans-form. The coordination of PdCl2 with 2-(o-hydroxyphenyl)-1H-imidazolines in solution was investigated by NMR spectroscopy. Palladium complexes composed of [Pd(Ln)2Cl2] (n = 1, 2, 3, 4, 6), [L5a]2[PdCl4] and [Pd(L5b)2], where L1 = 4,5-dihydro-2-phenyl-1H-imidazole (= 2-phenyl-1H-imidazoline), L2 = 2-(o-fluorophenyl)-1H-imidazoline, L3 = 2-(o-methylphenyl)-1H-imidazoline, L4 = 2-(o-tert-butylphenyl)-1H-imidazoline, L5a = 2-(o-hydroxyphenyl)-1H-imidazolinium, L5b = 2-(1H-imidazolin-2-yl) phenolate, and L6 = 2-(o-methylphenyl)-1H-imidazole, were synthesized and characterized by single crystal X-ray diffractometry.

Polymer-anchored oxovanadium(IV) complex for the oxidation of thioanisole, styrene and ethylbenzene

The ligand 2-(2′-hydroxyphenyl)-1H-imidazoline (Hpimin) was covalently linked to chloromethylated polystyrene (PS-Cl). This resin was then allowed to react with vanadyl sulfate to afford the polymer-anchored oxovanadium(IV) complex, PS-[VO(pimin)x], which was characterised using elemental analysis, IR and AFM. This catalyst was shown to catalyse the hydrogen peroxide-based oxidation of styrene, ethylbenzene and thioanisole. A maximum conversion of ethylbenzene (30.6%) and styrene (99.9%) was obtained by using 0.025 g of PS-[VO(pimin)x] and 4 equiv. of hydrogen peroxide at 80 °C after 6 h. The oxidation of thioanisole proceeded quantitatively (99.6%) within 4 h, with 0.025 g of PS-[VO(pimin)x], at room temperature with 2 equiv. of hydrogen peroxide. At the steady state, the main products from the oxidation of the various substrates were benzaldehyde (57.6%) > 1-phenylethane-1,2-diol (16.2%) > benzoic acid (7.1%) > styrene oxide (3.1%) for styrene; acetophenone (20.5%) > benzaldehyde (2.7%) for ethylbenzene; and methyl phenyl sulfoxide (67.4%) > methyl phenyl sulfone (31.9%) for thioanisole.

Synthesis, characterization and anti-diabetic effect of bis[(1-R-imidazolinyl)phenolato]oxovanadium(IV) complexes

The five-coordinate oxovanadium(IV) complexes; [VO(pimin)2] (1a), [VO(Etpimin)2] (2) and [VO(EtOHpimin)2] (3), were prepared by reacting the ligands; 2-(2′-hydroxyphenyl)-1H-imidazoline (piminH), 2-(2′-hydroxyphenyl)-1-eth

Study of synthesis of 2-(2-alkoxyphenyl)-1h-imidazoles. Comparison of oxidative aromatization reactions of imidazolines

The reaction of methyl salicylate with ethane-1,2-diamine has been used to prepare 2-(2-hydroxyphenyl)-1H-imidazoline. This compound was alkylated with alkyl halides to give five new 2-(2-alkoxyphenyl)-1H-imidazolines (alkyl = propyl, isopropyl, isobutyl,

Zeolite-catalyzed simple synthesis of different heterocyclic rings, part 2

A simple and environmentally friendly synthesis was developed for the preparation of 2-arylimidazoline derivatives and 2-arylbenzoxazole derivatives using a small pore size zeolite. The similar reaction was not applicable to the preparation of the sulfur-containing analogs cysteamine or 2-aminothiophenol, probably because of a disadvantageous reaction between the zeolite and the thio compound.

α1-Adrenoceptor agonists: The identification of novel α1A subtype selective 2′-heteroaryl-2-(phenoxymethyl)imidazolines

Novel 2′-heteroaryl-2-(phenoxymethyl)imidazolines have been identified as potent agonists of the cloned human α1-adrenoceptors in vitro. The nature of the 2′-heteroaryl group can have significant effects on the potency, efficacy, and subtype selectivity in this series. α1A Subtype selective agonists have been identified.