118474-44-5

Usage

Uses

Used in Pharmaceutical Industry:
4,5-Dimethyl-1H-imidazole-2-carboxaldehyde is utilized as an intermediate in the synthesis of various medications. Its role in this industry is pivotal due to its ability to contribute to the formation of complex drug molecules, enhancing the range of therapeutic options available.
Used in Organic Synthesis:
4,5-Dimethyl-1H-imidazole-2-carboxaldehyde also serves as a building block in organic synthesis, where it can be incorporated into the structure of other chemical compounds. Its versatility in forming different chemical entities makes it valuable in the creation of a wide array of products.
Used in Chemical Compound Preparation:
4,5-Dimethyl-1H-imidazole-2-carboxaldehyde is employed in the preparation of other chemical compounds, indicating its multifaceted utility in chemical research and development. Its capacity to be a part of new chemical entities underscores its importance in advancing chemical science and technology.

Upstream product

• 74483-00-4 4,5-Dimethyl-1-(1,1-diethoxymethyl)imidazole 
• 68-12-2 N,N-dimethyl-formamide 
• 2302-39-8 4,5-dimethylimidazole 

Downstream Products

• 115245-13-1 4,5-Dimethyl-2-(hydroxymethyl)imidazole 

Relevant academic research and scientific papers

Direct O-Acylation of Small Molecules Containing CO2(1-)---HN<--HO Units by a Distorted Amide: Enhancement of Amine Basicity by a Pendant Carboxylate in a Serine Protease Mimic

The kinetics of the reaction of two series of amino alcohols (ethanol amines and 2-hydroxymethylimidazoles) with a distorted amide were studied as models for the acylation of the serine proteases.The pH/logk2max profiles plateau above the amine pKa, indicating the basic form is active.In all cases, the reactions proceed by initial O-acylation to produce esters.With primary or secondary ethanolamines, subsequent O-->N acyl transfer occurs to give amides.In each series, a Bronsted relationship exists relating the increasing amine pKa with an increasing second-order rate constant for O-acylation.Amino alcohols containing a pendant carboxylate (e.g., serine and the 4(5)- derivative of 2-hydroxymethylimidazole) fit on the Bronsted plots exactly, which suggests the amine pKa controls the reactivity.The role of the carboxylate is to enhance the amine basicity by electrostatic/inductive means.This is particularly effective in solvents of reduced polarity (40percent and 80percent v/v, EtOH/H2O) since the above effects counteract the normal drop in amine pKa exhibited by the other amino alcohols that do not possess the CO2(1-).Both series exhibit low kinetic solvent isotope effects of between 1 and 2.In the imidazole alcohol series, as the amine pKa increases the kinetic solvent isotope effect tends to 1.0.This is discussed in terms of a possible involvement of direct nucleophilic attack of an ammonium alkoxide zwitterion on 1.

An Easily Introduced and Removed Protecting Group for Imidazole Nitrogen: A Convenient Route to 2-Substituted Imidazoles

Orthoamides (3-5) prepared from imidazoles and triethyl or trimethyl orthoformate are rapidly metalated at -40 deg C in THF or ether to give the corresponding 2-lithio anion which reacts with a variety of electrophiles.The dialkoxymethyl protecting group is readily hydrolyzed under neutral or acidic conditions at room temperature, giving the 2-substituted 1H-imidazole 1 (R = H, X = COOH, n-C4H9, COCH3, CHOHC6H5, C(CH3)OH-2-pyridyl,9-hydroxyfluorenyl, 1-hydroxycyclohex-2-enyl, C(OH)(C6H5)2; R = CH3, R' = H, X = CHO) and the tris(2-imidazolyl)phosphines (R = H, CH3, CH(CH3)2).A mechanism for the deprotection of 3 is proposed.