119717-21-4

Basic information

• Product Name: 4-[(R)-1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole
• Synonyms: (-)-4-[(R)-1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole;4-[(R)-1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole;Levomedetomidine;l-Medetomidine;MPV-1441;LevoMedetoMidine HCl
• CAS NO: 119717-21-4
• Molecular Formula: C13H16N2
• Molecular Weight: 200.28
• Product Categories: Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 119717-21-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 381.9±11.0 °C(Predicted)
• Appearance: /
• Density: 1.053±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethanol (Slightly), Methanol
• PKA: 13.89±0.10(Predicted)
• CAS DataBase Reference: 4-[(R)-1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(R)-1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole(119717-21-4)
• EPA Substance Registry System: 4-[(R)-1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole(119717-21-4)

Safety Data

• Hazardous Substances Data: 119717-21-4(Hazardous Substances Data)

Usage

Uses

α2-Adrenergic agonist; (-)-isomer of Medetomidine; sedative; analgesic.

Upstream product

• 21900-46-9 2,3-dimethylbenzoyl chloride 
• 138867-04-6 1-N,N-Dimethylsulfamoyl-2-(tert-butyldimethylsilyl)-5-(2,3-dimethylbenzoyl)imidazole 
• 86347-14-0 medetomidine 
• 86347-14-0 (+/-)-4(5)-<1-(2,3-Dimethylphenyl)ethyl-1H-imidazole> 
• 60907-90-6 1-(2,3-dimethylphenyl)ethanol 
• 60907-88-2 1-(1-chloroethyl)-2,3-dimethylbenzene 
• 18156-74-6 1-(Trimethylsilyl)imidazole 
• 176721-01-0 4-<(2,3-dimethylphenyl)hydroxymethyl>-1-(triphenylmethyl)imidazole 
• 176721-02-1 4-<(2,3-dimethylphenyl)carbonyl>-1-(triphenylmethyl)imidazole 
• 1021949-47-2 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 91130-37-9 1-isopropenyl-2,3-dimethyl-benzene 
• 156744-78-4 (2-(2,3-xylyl)-2-propanol) 
• 576-23-8 2,3-dimethylbromobenzene 

Relevant articles and documents

A novel and facile route for the synthesis of medetomidine as the α2-adrenoceptor agonist

Abstract: We report here a novel and facile method for the synthesis of (±)-4(5)-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (medetomidine) in a good yield in five steps. The method involves Wittig olefination of the phenylimidazolylketones, followed by a hydrogenation. We demonstrate that the Wittig alkenylation reaction provides a convenient step for the synthesis of medetomidine without requiring methylation and dehydration steps, which are problematic processes in the previous methods. Graphical Abstract: Novel route for the synthesis of medetomidine.[Figure not available: see fulltext.].

Preparation method of high-purity dexmedetomidine hydrochloride

The invention discloses a preparation method of high-purity dexmedetomidine hydrochloride, which comprises the following steps: by taking 1-(1-chloroethyl)-2, 3-dimethyl benzene and N-trimethylsilylimidazole as reaction raw materials, carrying out Friedel-Crafts alkylation reaction under the catalysis of an aprotic organic solvent and lewis acid, recrystallizing the obtained post-treated oil by using a specific solvent to obtain medetomidine solid, splitting by chiral acid, free of alkali and salt forming, and preparing the high-purity dexmedetomidine hydrochloride. According to the dexmedetomidine hydrochloride prepared by the preparation method disclosed by the invention, the splitting and refining times can be effectively reduced, the chemical purity and optical purity of the obtained dexmedetomidine hydrochloride can reach 100%, and the total yield is relatively high; and moreover, main starting materials are conventional industrial commodities, so that the preparation method is suitable for industrial production and has relatively high industrial application value.

Industrial preparation method of dexmedetomidine hydrochloride

The invention discloses an industrial preparation method of dexmedetomidine hydrochloride, and belongs to the field of medicines. The method comprises the following steps: directly carrying out a Friedel-Crafts alkylation reaction on initial raw materials comprising 1-(2,3-dimethylphenyl)ethanol not subjected to a chlorination (thionyl chloride) reaction and protected imidazole under the catalysis of a Lewis acid to obtain racemic dexmedetomidine, carrying out pre-resolution purification on the racemic dexmedetomidine through a chiral acid, carrying out chiral acid resolution and alkali dissociation, and adding a hydrochloric acid organic solvent to form a salt in order to obtain the dexmedetomidine hydrochloride. The method avoids use of the toxic and corrosive regent thionyl chloride, allows the above product with high chiral and chemical purity to be obtained and the yield to be high, and is suitable for industrial production.