TosMIC

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TosMIC[1]
TosMIC-2D-skeletal.png
TosMIC-3D-vdW.png
Names
IUPAC name
1-(isocyanomethylsulfonyl)-4-methylbenzene
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.048.293
Properties
C9H9NO2S
Molar mass 195.24 g mol−1
Melting point 109 to 113 °C (228 to 235 °F; 382 to 386 K)
Hazards
R-phrases R23/24/25
S-phrases S36/37 S45
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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[2] and imidazoles.[3] The versatility of TosMIC in orgnic synthesis has been documented.[4]

References[edit]

  1. ^ p-Toluenesulfonylmethyl isocyanide at Sigma-Aldrich
  2. ^ Keeri, Abdul Raheem; Gualandi, Andrea; Mazzanti, Andrea; Lewinski, Janusz; Cozzi, Pier Giorgio (2015-12-21). "Me2Zn-Mediated Catalytic Enantio- and Diastereoselective Addition of TosMIC to Ketones". Chemistry – A European Journal. 21 (52): 18949–18952. doi:10.1002/chem.201504362. ISSN 1521-3765. 
  3. ^ Hoogenboom, B. E.; Oldenziel, O. H.; van Leusen, A. M. (1977). "p-TOLYLSULFONYLMETHYL ISOCYANIDE". Org. Synth. 57: 102. ; Coll. Vol., 6, p. 987 
  4. ^ "Toluenesulphonylmethyl isocyanide (TOSMIC) and the van Leusen MCR". www.organic-chemistry.org. Retrieved 2017-02-28.