58379-86-5

Usage

Uses

Used in Organic Synthesis:
1-BENZYL-1-TOSYLMETHYL ISOCYANIDE is used as a building block in organic synthesis for the preparation of various organic molecules. Its reactivity and structural features contribute to the creation of a wide range of chemical compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-BENZYL-1-TOSYLMETHYL ISOCYANIDE is used as a reagent for the preparation of diverse biologically active compounds. Its potential applications in this field are attributed to its ability to facilitate the synthesis of molecules with therapeutic properties.
Used in Agrochemical Industry:
Similarly, 1-BENZYL-1-TOSYLMETHYL ISOCYANIDE finds use in the agrochemical industry, where it serves as a precursor in the synthesis of compounds with pesticidal or herbicidal activity. Its versatility in organic synthesis aids in the development of new agrochemical products.

InChI:InChI=1/C16H15NO2S/c1-13-8-10-15(11-9-13)20(18,19)16(17-2)12-14-6-4-3-5-7-14/h3-11,16H,12H2,1H3

Upstream product

• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 100-51-6 benzyl alcohol 

Downstream Products

• 65185-18-4 4-benzyl-5-furan-2-yl-oxazole 
• 65185-05-9 4-benzyl-5-thiophen-2-yl-oxazole 
• 65185-04-8 4-benzyl-5-(4-chloro-phenyl)-oxazole 
• 97388-58-4 2,7-diisocyano-1,8-diphenyl-2,7-ditosyloctane 
• 97388-61-9 2,6-diisocyano-1,7-diphenyl-2,6-ditosylheptane 
• 57697-74-2 4-benzyl-5-phenyl-oxazole 
• 1150560-61-4 C₁₃H₁₅NO 
• 1346013-66-8 2-benzyl-3-(4-chlorophenyl)-5-(1,3-dithiolan-2-ylidene)-5,6-dihydro-6-hydroxy-6-phenylcyclopenta[b]pyrrol-4(1H)-one 
• 1374979-72-2 C₁₈H₂₃NO₃ 
• 1374979-66-4 C₁₄H₁₄N₂O 
• 1374979-69-7 ethyl 5-benzyl-4-ethoxy-1H-pyrrole-3-carboxylate 
• 1444444-39-6 2-benzyl-2,3-dihydro-2-[(4-methylphenyl)sulfonyl]-1H-inden-1-imine 
• 1174070-12-2 2-[(2E)-3-phenylprop-2-en-1-yl]benzonitrile 
• 936800-16-7 (E)-2-(3-phenyl-prop-1-en-1-yl)benzonitrile 

Relevant academic research and scientific papers

1-Trifluoromethylisoquinolines from α-Benzylated Tosylmethyl Isocyanide Derivatives in a Modular Approach

The preparation of various 1-trifluoromethylisoquinolines from α-benzylated tosylmethyl isocyanide derivatives and the commercial Togni reagent using a radical cascade is reported. The starting isocyanides are readily prepared in a modular sequence from commercial tosylmethyl isocyanide via sequential double α-alkylation, and the radical reaction proceeds under mild conditions with high efficiency without any transition-metal catalyst via electron catalysis. This valuable protocol has been successfully applied to the total synthesis of CF3-mansouramycin B.

Alkenyl Isocyanide Conjugate Additions: A Rapid Route to γ-Carbolines

Isocyanides are exceptional building blocks, the wide deployment of which in multicomponent and metal-insertion reactions belies their limited availability. The first conjugate addition/alkylation to alkenyl isocyanides is described, which addresses this deficiency. An array of organolithiums, magnesiates, enolates, and metalated nitriles add conjugately to β- and β,β-disubstituted arylsulfonyl alkenyl isocyanides to rapidly assemble diverse isocyanide scaffolds. The intermediate metalated isocyanides are efficiently trapped with electrophiles to generate substituted isocyanides incorporating contiguous tri- and tetra-substituted centers. The substituted isocyanides are ideally functionalized for elaboration into synthetic targets as illustrated by the three-step synthesis of γ-carboline N-methyl ingenine B.

Sulfination of Alcohols with p-Toluenesulfonylmethyl Isocyanide under Metal-Free Conditions: A Mitsunobu Approach

A Mitsunobu approach for the synthesis of sulfinate esters by direct nucleophilic substitution of alcohols is described. The salient features of this strategy include neutral and metal-free conditions for the rapid synthesis of sulfinates in high yields. The present protocol using p-toluenesulfonylmethyl isocyanide (TosMIC) and the triphenylphosphine (TPP)/diisopropyl azodicarboxylate (DIAD) reagent system represents the general synthetic route to this important class of compounds. (Figure presented.).

Discovery of a type III inhibitor of LIM kinase 2 that binds in a DFG-out conformation

The first allosteric, type III inhibitor of LIM-kinase 2 (LIMK2) is reported. A series of molecules that feature both an N-phenylsulfonamide and tertiary amide were not only very potent at LIMK2 but also were extremely selective against a panel of other k

Discovery of a Type III Inhibitor of LIM Kinase 2 That Binds in a DFG-Out Conformation

The first allosteric, type III inhibitor of LIM-kinase 2 (LIMK2) is reported. A series of molecules that feature both an N-phenylsulfonamide and tertiary amide were not only very potent at LIMK2 but also were extremely selective against a panel of other k

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