35342-89-3

Usage

Structure

A derivative of imidazole with a trimethylsilyl group attached to the second carbon atom of the imidazole ring.

Common uses

As a base in organic reactions, particularly in the synthesis of various organic compounds.

Reactivity

Strong nucleophile that can facilitate reactions such as alkylation, acylation, and deprotection of functional groups in organic molecules.

Applications in peptide synthesis

Used as a deprotection agent for certain protecting groups.

Catalytic properties

Acts as a catalyst in various chemical reactions due to its basic properties and stability.

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 30148-21-1 ethyl 1-methyl-1H-imidazole-2-carboxylate 
• 154475-18-0 isopropyl 1-methylimidazole-2-carboxylate 
• 154475-20-4 benzyl 1-methylimidazole-2-carboxylate 
• 62366-53-4 methyl 1-methyl-1H-imidazole-2-carboxylate 
• 616-47-7 1-methyl-1H-imidazole 
• 1066-40-6 Trimethylsilanol 
• 420-56-4 trimethylsilyl fluoride 
• 80679-27-2 tris(1-methylimidazol-2-yl)phosphine 
• 1333154-46-3 1,2-bis(1-methylimidazol-2-ylphenylphosphino)ethane 
• 62366-54-5 phenyl 1-methylimidazole-2-carboxylate 

Relevant academic research and scientific papers

Investigation of carbon-2 substituted imidazoles and their corresponding ionic liquids

The functionality at the C-2 position of the imidazole ring plays a key role in defining the chemical properties of the imidazoles and their corresponding ionic liquids. Imidazoles 1-6 with different C-2 functionality were synthesized and their corresponding ionic liquids were systematically investigated. Based on their physical properties the six imidazoles can be divided into three groups. (1) The imidazoles 2 and 3 are capable of self-polymerization to form poly(ionic liquid)s, and they are characterized with a strong leaving group at the C-2 position. (2) The imidazoles 4 and 5 can form ionic liquids, but they are very sensitive to moisture. (3) The imidazoles 1 and 6 can form stable ionic liquids, and their stabilities were influenced by the electronic effects of the substituents at the C-2 position.

N-phosphorylated imidazolium salts as precursors to 2- and 5-phosphorylated imidazoles and new imidazol-2-ylidenes featuring the PNCN unit

It has been experimentally proven that the reaction of 1- or 1,2-disubstituted imidazoles with diorganylphosphorus(III) halides proceeds via initial formation of N-phosporylated imidazolium salts. Treatment of these salts with strong bases results in phosphorylation of the parent imidazoles at the 2- or 5-positions, correspondingly. In a previous case, imidazol-2-ylidenes are formed as intermediates. With both N1 and N3 atoms bearing sterically demanding or/and π-donating groups, deprotonation of 1,3-disubstituted imidazolium salts with NaN(SiMe3)2 afforded new stable N-phosphorus-substituted Arduengo-type carbenes.

Transfer of Alkoxycarbonyl from Alkyl Imidazolium-2-carboxylates to Benzyl Alcohol, a Cyclohexanone Enamine and Diethylamine

Alkylimidazole-2-carboxylates may be alkylated with methyl triflate to give the corresponding N-methylimidazolium salts.These salts react with benzyl alcohol in the presence of 1,4-diazabicyclooctane, with 1-(pyrrolidin-1-yl)cyclohexene and with diethylamine to give benzyl alkyl carbonates, an enamino ester and a urethane respectively; in one case a tetrahedral intermediate is observed.The corresponding phenyl ester was consumed without attack by benzyl alcohol at the carbonyl group.A 2-cyanoimidazolium salt underwent similar ill-defined consumption whereas a 2-dimethylaminocarbonyl derivative remained unchanged. 2-Methylsulfonylimidazolium salts suffered attack by benzyl alcohol at the ring C-2.