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

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

Uses

Used in Medicinal Chemistry:
1H-Imidazole, 4,5-dihydro-2-(2-fluorophenyl)is used as a chemical intermediate for the development of drugs targeting various biological processes. Its unique structure allows for the design of novel compounds with potential therapeutic effects.
Used in Organic Synthesis:
As a building block, 1H-Imidazole, 4,5-dihydro-2-(2-fluorophenyl)is utilized in the synthesis of other organic compounds, contributing to the creation of new molecules with specific properties and applications.
Used in Pharmacological Research:
Due to its potential biological activity, 1H-Imidazole, 4,5-dihydro-2-(2-fluorophenyl)is employed in pharmacological research to explore its interactions with biological systems and to understand its effects on various physiological processes.
Used in Biochemical Studies:
1H-IMidazole, 4,5-dihydro-2-(2-florophenyl)may also be used in biochemical studies to investigate its role in enzymatic reactions or to assess its binding affinity to specific biological targets, providing insights into its potential as a therapeutic agent or a tool in biochemical research.

Upstream product

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

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.

One-pot synthesis of imidazolines from aldehydes: detailed study about solvents and substrates

Imidazolines were prepared in one-pot operation from aldehydes and diamines through oxidation of aminal intermediates by NBS. This method could be applied to various aromatic and aliphatic aldehydes and N-nonsubstituted and N-monosubstituted 1,2-diamines. Furthermore, it was found that CH2Cl2 could be altered to TBME, a more environmentally friendly solvent, in the reaction using N-nonsubstituted 1,2-diamines. The reaction conditions were very mild and chemoselective.

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.

Reactions of some ortho and para halogenated aromatic nitriles with ethylenediamine: Selective synthesis of imidazolines

The reaction of ethylenediamine (EDA) with ortho and/or para halogenated benzonitriles did not lead to the imidazolines expected: a competitive aromatic nucleophilic substitution (SNAr) was observed instead. The selective synthesis of these imidazolines was performed by nucleophilic addition of EDA to thiobenzamide derivatives. The difference in reactivity between the nitrile and thioamide derivatives was estimated by a frontier orbital approach at the RHF/6-31G** level which predicted a greater reactivity of substituted thiobenzamides towards the nucleophilic addition of EDA.

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

RING INTERCONVERSION BETWEEN A 7-MEMBERED RING (2,3-DIHYDRO-1,4-BENZODIAZEPINE) AND A 14-MEMBERED RING (2,3,9,10-DIBENZO-1,5,8,12-TETRA-AZACYCLOTETRADECA-4,11-DIENE)

Structure elucidation of the macrocyclic ligand 6 and interconversion to the benzodiazepine 4 is reported.Also, a versatile synthesis of the macrocyclic ligands 6 and 13 is described.