9556. Tosylmethyl Isocyanide

Nomenclature

CAS number: 36635-61-7
1-[(Isocyanomethyl)sulfonyl]-4-methylbenzene; (4-methylphenylsulfonyl)methyl isocyanide; p-toluenesulfonylmethyl isocyanide; TosMIC.
C9H9NO2S; mol wt 195.24.
C 55.37%, H 4.65%, N 7.17%, O 16.39%, S 16.42%.

Description and references

Isonitrile reagent with reversed polarity; serves as a carbonyl anion equivalent in organic synthesis. Prepn: U. Schllkopf et al., Ann. 766, 130 (1972); A. M. van Leusen et al., Tetrahedron Lett. 13, 2367 (1972); B. E. Hoogenboom et al., Org. Synth. 57, 102 (1977). Review of applications in organic synthesis: C. Lamberth, J. Prakt. Chem. Chem.-Ztg. 340, 483-485 (1998); V. K. Tandon, S. Rai, Sulfur Rep. 24, 307-385 (2003).

Chemical structure

Properties

Crystals from methanol, mp 116-117° (dec).

Use

Versatile synthon in organic chemistry, esp in the synthesis of heterocyclic compds.