253453-91-7

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-1-methyl-1H-imidazole is used as a pharmaceutical intermediate for the synthesis of various drugs and drug candidates. Its unique chemical structure allows it to be a key component in the development of new medications, particularly those targeting specific biological pathways or receptors.
Used in Chemical Catalysts:
In the field of catalysis, 2-Chloro-1-methyl-1H-imidazole serves as a ligand for transition metal catalysts. Its ability to form stable complexes with metal ions makes it a valuable component in the design and synthesis of catalysts for various chemical reactions, enhancing their efficiency and selectivity.
Used in Molecular Functional Materials:
2-Chloro-1-methyl-1H-imidazole is also utilized in the development of molecular functional materials. Its structural diversity and potential for modification make it a promising candidate for applications in areas such as sensors, optoelectronics, and molecular devices.

InChI:InChI=1/C4H5ClN2/c1-7-3-2-6-4(7)5/h2-3H,1H3

Upstream product

• 616-47-7 1-methyl-1H-imidazole 

Downstream Products

• 807614-69-3 (2-chloro-3-methyl-3H-imidazol-4-yl)(4-chlorophenyl)methanone 
• 869002-70-0 (3-fluoro-phenyl)-(2-chloro-3-methyl-3H-imidazol-4-yl)-methanol 
• 869002-62-0 2-chloro-1-methyl-1H-imidazole-5-carbaldehyde 
• 869002-61-9 2-Chloro-3-methyl-3H-imidazole-4-carboxylic acid 
• 1258411-57-2 C₁₂H₁₁Cl₂N₃O 
• 1393880-04-0 1-benzyl-4-(1-methyl-1H-imidazol-2-yl)-1H-pyrazole 

Relevant academic research and scientific papers

Highly regioselective C-5 alkynylation of imidazoles by one-pot sequential bromination and Sonogashira cross coupling

A variety of 2-substituted 5-alkynyl-1H-imidazoles were easily prepared by a one-pot sequential procedure involving a highly regioselective electrophilic C-5 bromination of 1,2-dimethyl-1H-imidazole, 2-chloro-1-methyl-1H-imidazole, and 2-aryl-1-methyl-1H-imidazoles, followed by an efficient palladium/copper co-catalyzed Sonogashira-type alkynylation.

Synthesis of enantiomerically pure 2-heteroaromatic-substituted 1,2-amino alcohols from chiral tert-butanesulfinyl aldimines

Nine R/S pairs of 2-heteroaromatic-substituted 1,2-amino alcohols were synthesized through 1,2-nucleophilic addition between chiral N-(tert-butylsulfinyl)imines and heteroaromatic carbanions. In most cases, the R S-isomer of N-(tert-butylsulfinyl)imines afforded the R amino alcohol from deprotection of the major diastereomer, and S S-imines afforded the S product. In general, this procedure allows for the preparation of a variety of enantiomeric pairs of 2-heteroaromatic-substituted 1,2-amino alcohols on a practical scale (>10 g) in two steps in good yields.

Lewis basicity modulation of N-heterocycles: A key for successful cross-metathesis

Cross-metathesis involving N-heteroaromatic olefinic derivatives is disclosed. The introduction of an appropriate substituent on the heteroaromatic ring decreases the Lewis basicity of the nitrogen atom, thus preventing the deactivation of the ruthenium-centered catalyst. The reaction is quite general in terms of both N-heterocycles and olefinic partners.

Scalable synthesis of imidazole derivatives

Imidazole derivatives, compositions containing them, methods of preparing them, including regioselective scale-up synthetic methods, and methods of using them.

A scalable synthesis of a histamine H3 receptor antagonist

Starting from 1-methylimidazole, a concise, scalable, three-step synthesis of the title compound is described. The required 2-chloroimidazole was prepared in very good yield by halogen-metal exchange between the 2-lithio derivative and hexachloroethane.

Tetrahalogenomethanes: Simple reagents for the synthesis of monohalogenated and mixed dihalogenated aromatic heterocycles via metal-halogen exchange from lithium compounds

Tetrabromo- or tetrachloromethane and 2-lithio derivatives of aromatic heterocycles rapidly produce the corresponding 2-bromo or 2-chloro derivatives in high yields through a metal-halogen exchange mechanism. This kind of reaction was also used to obtain, in good yields, 5-bromo-2-chlorothiazole and 5-bromo-2-chloro-N-methylimidazole.

A new synthesis of chloroheterocycles via metal-halogen exchange between trichloroacetyl derivatives and heteroaromatic lithium and Grignard reagents

The reaction between 2-lithio derivatives of aromatic azaheterocycles and trichlorocetyl derivatives rapidly produces the corresponding 2-chloro derivatives in high yields through a metal-halogen exchange mechanism. The use of ethyl trichloroacetate can give better results with respect to those obtained with trichloroacetyl chloride, which probably involves dichloroketene formation. The reaction with Grignard reagents is more complex: in fact, 2-benzothiazolylmagnesium chloride with ethyl trichloroacetate or trichloroacetyl chloride gives 2-chlorobenzothiazole together with considerable amounts of ethyl 1,3-benzothiazole-2-carboxylate or 2-benzothiazolyl dichloromethyl ketone, respectively.

INTRODUCTION OF SUBSTITUENTS INTO 5-MEMBERED AZA-HETEROAROMATICS

With emphasis on mono- and regio-selectively, methods for introduction of substituents at nitrogen and carbon atoms of 5-membered aza-heteroaromatics have been developed.The methods involve application of activation and of assistant groups for direction and protection.Activation has been achieved by the use of quaternary azolium ions and azol-N-oxides as reactive intermediates.If necessary, the N-oxides were further activated by alkylation or acylation.