Chemistry:TosMIC

TosMIC

Names
Preferred IUPAC name 1-(Isocyanomethanesulfonyl)-4-methylbenzene
Other names Toluenesulfonylmethyl isocyanide
Identifiers
CAS Number	36635-61-7 Y
3D model (JSmol)	Interactive image
ChemSpider	142204 Y
EC Number	36635-61-7
PubChem CID	161915
UNII	C35FD6OLH8 Y
InChI InChI=1S/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3 Y Key: CFOAUYCPAUGDFF-UHFFFAOYSA-N Y InChI=1/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3 Key: CFOAUYCPAUGDFF-UHFFFAOYAC
SMILES O=S(=O)(c1ccc(cc1)C)C[N+]#[C-]
Properties
Chemical formula	C9H9NO2S
Molar mass	195.24 g·mol−1
Melting point	109 to 113 °C (228 to 235 °F; 382 to 386 K)
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H301, H311, H331
GHS precautionary statements	P261, P264, P270, P271, P280, P301+310, P302+352, P304+340, P311, P312, P321, P322, P330, P361, P363, P403+233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

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 in the Van Leusen reaction which is used to convert ketones to nitriles or 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 pK_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.