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TosMIC

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TosMIC[1]
Names
IUPAC name
1-(isocyanomethylsulfonyl)-4-methylbenzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.048.293 Edit this at Wikidata
  • InChI=1S/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3 checkY
    Key: CFOAUYCPAUGDFF-UHFFFAOYSA-N checkY
  • InChI=1/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3
    Key: CFOAUYCPAUGDFF-UHFFFAOYAC
  • O=S(=O)(c1ccc(cc1)C)C[N+]#[C-]
Properties
C9H9NO2S
Molar mass 195.24 g mol−1
Melting point 109 to 113 °C (228 to 235 °F; 382 to 386 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Toluenesulfonylmethyl isocyanide or TOSMIC is an organic compound with the formula CH3C6H4SO2CH2NC. The molecule contains both sulfonyl and isocyanide groups. It is a colourless solid that unlike many isocyanides, is odorless. It is prepared by dehydration of the related formamide derivative. It is used in the Van Leusen reaction which is used to convert aldehydes to nitriles or in the preparation of oxazoles and imidazoles.[2]

References

  1. ^ p-Toluenesulfonylmethyl isocyanide at Sigma-Aldrich
  2. ^ Hoogenboom, B. E.; Oldenziel, O. H.; van Leusen, A. M. (1977). "p-TOLYLSULFONYLMETHYL ISOCYANIDE". Organic Syntheses. 57: 102{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 6, p. 987.