58379-81-0

Usage

Uses

Used in Organic Synthesis:
1-Ethyl-1-tosylmethyl isocyanide is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides.
Used in Coordination Chemistry:
As a ligand, 1-ethyl-1-tosylmethyl isocyanide is employed in the formation of coordination compounds, which have potential applications in catalysis, materials science, and other areas.
Used in the Synthesis of Complex Organic Molecules:
1-ETHYL-1-TOSYLMETHYL ISOCYANIDE serves as a building block in the assembly of complex organic molecules, facilitating the creation of novel chemical structures with unique properties and potential applications.
Caution:
Due to its high toxicity, 1-ethyl-1-tosylmethyl isocyanide should be handled with extreme care to prevent adverse health effects and environmental contamination. Proper safety measures and protective equipment are essential when working with this chemical compound.

InChI:InChI=1/C11H13NO2S/c1-4-11(12-3)15(13,14)10-7-5-9(2)6-8-10/h5-8,11H,4H2,1-2H3

Upstream product

• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 75-03-6 ethyl iodide 
• 74-96-4 ethyl bromide 

Downstream Products

• 90704-16-8 1,4'-Bis-benzenesulfonyl-2'-ethyl-5-methyl-1H,1'H-[3,3']bipyrrolyl 
• 65185-02-6 4-ethyl-5-phenyl-oxazole 
• 1444444-45-4 2,3-dihydro-2-ethyl-5-fluoro-2-[(4-methylphenyl)sulfonyl]-1H-inden-1-imine 
• 1444444-33-0 2,3-dihydro-2-ethyl-2-[(4-methylphenyl)sulfonyl]-1H-inden-1-imine 
• 1444444-48-7 2,3-dihydro-2-ethyl-5-methoxy-2-[(4-methylphenyl)sulfonyl]-1H-inden-1-imine 
• 1414874-49-9 tert-butyl (2-(5-(benzylcarbamoyl)-4-ethyl-1H-imidazol-1-yl)phenyl)carbamate 
• 1360871-21-1 3-ethyl-4-phenylimidazo[1,5-a]quinoxaline 
• 1146696-14-1 5-(4-(difluoromethyl)phenyl)-4-ethyloxazole 
• 1146695-95-5 4-ethyl-5-(2-fluoro-4-(trifluoromethyl)phenyl)oxazole 
• 1146695-98-8 5-(4-bromophenyl)-4-ethyloxazole 
• 1146695-85-3 4-ethyl-5-[4-(trifluoromethyl)phenyl]oxazole 
• 65185-03-7 5-(4-chloro-phenyl)-4-ethyl-oxazole 

Relevant academic research and scientific papers

Catalytic Enantio- and Diastereoselective Mannich Addition of TosMIC to Ketimines

Chiral amines bearing a stereocenter in the α position are ubiquitous compounds with many applications in the pharmaceutical and agrochemical sectors, as well as in catalysis. Catalytic asymmetric Mannich additions represent a valuable method to access such compounds in enantioenriched form. This work reports the first enantio- and diastereoselective addition of commercially available p-toluenesulfonylmethyl isocyanide (TosMIC) to ketimines, affording 2-imidazolines bearing two contiguous stereocenters, one of which is fully-substituted, with high yields and excellent stereocontrol. The reaction, catalyzed by silver oxide and a dihydroquinine-derived N,P-ligand, is broad in scope, operationally simple, and scalable. Derivatization of the products provides enantioenriched vicinal diamines, precursors to NHC ligands and sp3-rich heterocyclic scaffolds. Computations are used to understand catalysis and rationalize stereoselectivity.

Synthesis of Substituted Pyrroles via Copper-Catalyzed Cyclization of Ethyl Allenoates with Activated Isocyanides

A new method for the synthesis of di- and trisubstituted pyrroles via copper-catalyzed cyclization of ethyl allenoates with activated isocyanides has been developed. In contrast to related annulation reactions previously reported, this new process features a skeletal rearrangement in which the aryl sulfonyl moiety, which functions as the electron-withdrawing group in the α-carbon of the isocyanide, was found to migrate to the γ-carbon of the starting allenoate in the final product for the first time.

One-pot Van Leusen synthesis of 4,5-disubstituted oxazoles in ionic liquids

An efficient and mild protocol for the preparation of 4,5-disubstituted oxazoles through an improved one-pot van Leusen oxazole synthesis in ionic liquids is described. The oxazole products were prepared from tosylmethyl isocyanide (TosMIC), aliphatic hal

Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-Diarylimidazoles

The synthesis and the pharmacological activity of a series of 1,5-diarylimidazoles developed as potent and selective cyclooxygenase-2 (COX-2) inhibitors are described. The new compounds were evaluated both in vitro (COX-1 and COX-2 inhibition in human whole blood) and in vivo (carrageenan-induced paw edema, air-pouch, and hyperalgesia tests). Modification of all the positions of two regioisomeric imidazole cores led to the identification of 4-[4-chloro-5-(3-fluoro4-methoxyphenyl)imidazol-1-yl]benzenesulfonamide (UR-8880, 51f) as the best candidate, which is now undergoing Phase I clinical trials.