TosMIC

Chemical compound From Wikipedia, the free encyclopedia

TosMIC (toluenesulfonylmethyl isocyanide) 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 to convert ketones to nitriles (Van Leusen reaction) and in the preparation of oxazoles[2] and imidazoles.[3] The versatility of TosMIC in organic synthesis has been documented.[4] It is a fairly strong carbon acid, with an estimated pKa of 14 (compared to 29 for methyl tolyl sulfone), the isocyano group acting as an electron acceptor of strength comparable to an ester group.[5] TosMIC has also been used as a ligand in transition metal complexes due to the ligating nature of its isocyanide group.[6][7]

Quick facts Names, Identifiers ...
TosMIC[1]
Names
Preferred IUPAC name
1-(Isocyanomethanesulfonyl)-4-methylbenzene
Other names
Toluenesulfonylmethyl isocyanide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.048.293 Edit this at Wikidata
EC Number
  • 36635-61-7
UNII
  • 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)
Hazards
GHS labelling:
GHS06: Toxic
Danger
H301, H311, H331
P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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