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

Uses

Reactant for synthesis of:Polymer-anchored oxovanadium(IV) complexα1-Adrenoceptor agonistsReactant for: Oxidative aromatization reactions of imidazolinesIntramolecular nitrogen-phosphorous interactions of phosphate esters

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

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

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 
• 912338-40-0 2-(2-ethoxyphenyl)-1H-imidazole 
• 912338-42-2 2-(2-isopropoxyphenyl)-1H-imidazole 
• 52091-35-7 2-(2-methoxyphenyl)-1H-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.