58379-81-0

Basic information

• Product Name: 1-ETHYL-1-TOSYLMETHYL ISOCYANIDE
• Synonyms: 1-ETHYL-1-TOSYLMETHYL ISOCYANIDE;Benzene, 1-[(1-isocyanopropyl)sulfonyl]-4-methyl-;1-((1-Isocyanopropyl)sulfonyl)-4-methylbenzene
• CAS NO: 58379-81-0
• Molecular Formula: C₁₁H₁₃NO₂S
• Molecular Weight: 223.29
• Mol File: 58379-81-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-ETHYL-1-TOSYLMETHYL ISOCYANIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ETHYL-1-TOSYLMETHYL ISOCYANIDE(58379-81-0)
• EPA Substance Registry System: 1-ETHYL-1-TOSYLMETHYL ISOCYANIDE(58379-81-0)

Safety Data

• Hazardous Substances Data: 58379-81-0(Hazardous Substances Data)

Usage

General Description

1-ethyl-1-tosylmethyl isocyanide is a chemical compound with the molecular formula C11H13NO2S and a molar mass of 223.29 g/mol. It is a derivative of isocyanide, which contains an isocyanide group (-N≡C) attached to a tosylmethyl and ethyl group. 1-ETHYL-1-TOSYLMETHYL ISOCYANIDE is primarily used in organic synthesis, particularly in the preparation of various pharmaceuticals and agrochemicals. It is also used as a ligand in coordination chemistry and as a building block in the synthesis of complex organic molecules. 1-ethyl-1-tosylmethyl isocyanide is known to be highly toxic and should be handled with care.

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

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

Downstream Products

• 65185-02-6 4-ethyl-5-phenyl-oxazole 
• 1444444-48-7 2,3-dihydro-2-ethyl-5-methoxy-2-[(4-methylphenyl)sulfonyl]-1H-inden-1-imine 
• 1444444-33-0 2,3-dihydro-2-ethyl-2-[(4-methylphenyl)sulfonyl]-1H-inden-1-imine 
• 1444444-45-4 2,3-dihydro-2-ethyl-5-fluoro-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 
• 90704-16-8 1,4'-Bis-benzenesulfonyl-2'-ethyl-5-methyl-1H,1'H-[3,3']bipyrrolyl 
• 65185-03-7 5-(4-chloro-phenyl)-4-ethyl-oxazole 

Relevant articles and documents

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.

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