TosMIC (toluenesulfonylmethyl isocyanide) is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula CH₃C₆H₄SO₂CH₂NC. The molecule contains both sulfonyl and

isocyanide An isocyanide (also called isonitrile or carbylamine) is an organic compound with the functional group –. It is the isomer of the related nitrile (–C≡N), hence the prefix is ''isocyano''.IUPAC Goldboo''isocyanides''/ref> The organic fragme ...

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. and imidazoles. The versatility of TosMIC in organic synthesis has been documented. It is a fairly strong carbon acid, with an estimated p''K''_a of 14 (compared to 29 for methyl tolyl sulfone), the isocyano group acting as an electron acceptor of strength comparable to an ester group.

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