124314-68-7

Basic information

• Product Name: 1H-IMidazole, 4,5-dihydro-2-(2-florophenyl)-
• Synonyms: 1H-IMidazole, 4,5-dihydro-2-(2-florophenyl)-;2-(2-fluorophenyl)-4,5-dihydro-1H-Imidazole
• CAS NO: 124314-68-7
• Molecular Formula: C₉H₉FN₂
• Molecular Weight: 164.1795632
• Mol File: 124314-68-7.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-IMidazole, 4,5-dihydro-2-(2-florophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-IMidazole, 4,5-dihydro-2-(2-florophenyl)-(124314-68-7)
• EPA Substance Registry System: 1H-IMidazole, 4,5-dihydro-2-(2-florophenyl)-(124314-68-7)

Safety Data

• Hazardous Substances Data: 124314-68-7(Hazardous Substances Data)

Usage

General Description

1H-Imidazole, 4,5-dihydro-2-(2-fluorophenyl)- is a chemical compound with the formula C10H10FN3. It is a derivative of imidazole, a five-membered aromatic ring with two nitrogen atoms. The compound contains a fluorine-substituted phenyl group attached to the imidazole ring. 1H-IMidazole, 4,5-dihydro-2-(2-florophenyl)- has potential applications in the field of medicinal chemistry, particularly in the development of drugs targeting various biological processes. It is also used as a building block in the synthesis of other organic compounds. Additionally, it may exhibit biological activity and could be utilized for research purposes in the fields of pharmacology and biochemistry.

Upstream product

• 394-35-4 methyl 2-fluorobenzoate 
• 107-15-3 ethylenediamine 
• 394-47-8 2-fluorobenzonitrile 
• 446-52-6 2-Fluorobenzaldehyde 
• 75907-82-3 2-fluorobenzothioamide 

Downstream Products

• 1245730-23-7 trans-dichlorobis[(2-o-fluorophenyl)-1H-imidazoline]palladium(II) 

Relevant articles and documents

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.

A mild and efficient one-pot synthesis of 2-dihydroimidazoles from aldehydes

The reactions of various aldehydes and 1,2-diamines followed by NXS treatment proceed at 0°C-rt to give the corresponding dihydroimidazoles in high yields. The reaction is mild, and many functional groups such as halogens, nitriles, and esters can exist.

Synthesis and pharmacological evaluation of imidazoline sites I1 and I2 selective ligands

Several series of 2-aryl or heterocyclic-imidazoline compounds have been prepared and evaluated in vitro as imidazoline sites (I1 and I2) and α-adrenergic (α1 and α2) receptor ligands. Their pKi values indicate that linkage of the imidazoline moiety at the 2-position with an aromatic substituent dramatically decreases α-adrenergic affinity. I1 sites are more accessible by phenyl imidazolines substituted by a methyl or a methoxy group at the ortho or meta position. Indeed, 2-(2′-methoxyphenyl)-imidazoline (17) is one of the best I1 ligands ever reported (pKi=8.53 and I1/I2>3388). On the other hand, I2 selectivity increases in the presence of a methyl group in the para position. The original compound, 2-(3′-fluoro-4′-tolyl)-imidazoline (31) is a new potent ligand for the I2 sites with high selectivity (pKi=8.53 and I2/I1>3388). Copyright