1565-39-5

Basic information

• Product Name: 2-(4 5-DIHYDRO-1H-IMIDAZOL-2-YL)PHENOL
• Synonyms: 2-(4,5-Dihydro-1H-imidazol-2-yl)phenol 97%;6-imidazolidin-2-ylidenecyclohexa-2,4-dien-1-one;2-(2-Hydroxyphenyl)-2-imidazoline;o-2-Imidazolin-2-yl-phenol
• CAS NO: 1565-39-5
• Molecular Formula: C₉H₁₀N₂O
• Molecular Weight: 162.1885
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Imidazolines/Imidazolidines
• Mol File: 1565-39-5.mol
• Article Data: 13

Chemical Properties

• Melting Point: 205-209 °C
• Boiling Point: 367.1°Cat760mmHg
• Flash Point: 173.9°C
• Appearance: /
• Density: 1.217g/cm³
• Vapor Pressure: 1.39E-05mmHg at 25°C
• Refractive Index: 1.593
• PKA: 7.69±0.35(Predicted)
• CAS DataBase Reference: 2-(4 5-DIHYDRO-1H-IMIDAZOL-2-YL)PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4 5-DIHYDRO-1H-IMIDAZOL-2-YL)PHENOL(1565-39-5)
• EPA Substance Registry System: 2-(4 5-DIHYDRO-1H-IMIDAZOL-2-YL)PHENOL(1565-39-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 2
• Hazardous Substances Data: 1565-39-5(Hazardous Substances Data)

Usage

Description

2-(4,5-Dihydro-1H-Imidazol-2-yl)Phenol is an organic compound characterized by its unique chemical structure, which features a phenol group and an imidazol ring. 2-(4 5-DIHYDRO-1H-IMIDAZOL-2-YL)PHENOL has potential applications in various fields due to its chemical properties and reactivity.

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

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

Downstream Products

• 52091-35-7 2-(2-methoxyphenyl)-1H-imidazole 
• 912338-42-2 2-(2-isopropoxyphenyl)-1H-imidazole 
• 912338-40-0 2-(2-ethoxyphenyl)-1H-imidazole 
• 78584-00-6 2-(2-methoxyphenyl)-4,5-dihydro-1H-imidazole 
• 912338-38-6 2-(2-sec-butoxyphenyl)-1H-imidazoline 
• 912338-35-3 2-(2-propoxyphenyl)-1H-imidazoline 
• 78584-01-7 2-(2-ethoxyphenyl)-1H-imidazoline 
• 912338-39-7 2-(2'-benzyloxyphenyl)-4,5-dihydroimidazole 
• 912338-37-5 2-(2-isobutoxyphenyl)-1H-imidazoline 
• 78584-02-8 2-(o-Butoxyphenyl)-Δ²-imidazolin 
• 52755-90-5 2’-(2-hydroxyphenyl)imidazole 

Relevant articles and documents

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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.

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.