TosMIC

TosMIC[1]
Names
	IUPAC name 1-(Isocyanomethylsulfonyl)-4-methylbenzene
	Other names Toluenesulfonylmethyl isocyanide
Identifiers
CAS Number	36635-61-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	142204 ;
ECHA InfoCard	100.048.293
PubChem CID	161915;
UNII	C35FD6OLH8 ;
CompTox Dashboard (EPA)	DTXSID90190101 ;
	InChI InChI=1S/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3 Key: CFOAUYCPAUGDFF-UHFFFAOYSA-N ; 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
R-phrases (outdated)	R23/24/25
S-phrases (outdated)	S36/37 S45
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	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 aldehydes to nitriles or 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 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.[5]

References

p-Toluenesulfonylmethyl isocyanide at Sigma-Aldrich
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. PMID 26549317.
Hoogenboom, B. E.; Oldenziel, O. H.; van Leusen, A. M. (1977). "p-TOLYLSULFONYLMETHYL ISOCYANIDE". Organic Syntheses. 57: 102.; Collective Volume, 6, p. 987
"Toluenesulphonylmethyl isocyanide (TOSMIC) and the van Leusen MCR". www.organic-chemistry.org. Retrieved 2017-02-28.
van Leusen, Albert M.; van Leusen, Daan; Czakó, Barbara (2008-09-15), "p-Tolylsulfonylmethyl Isocyanide", Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, Ltd, doi:10.1002/047084289x.rt150.pub2, ISBN 978-0471936237

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[1] -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. PMID 26549317.

[3] Hoogenboom, B. E.; Oldenziel, O. H.; van Leusen, A. M. (1977). "p-TOLYLSULFONYLMETHYL ISOCYANIDE". Organic Syntheses. 57: 102.; Collective Volume, 6, p. 987

[4] "Toluenesulphonylmethyl isocyanide (TOSMIC) and the van Leusen MCR". www.organic-chemistry.org. Retrieved 2017-02-28.

[5] van Leusen, Albert M.; van Leusen, Daan; Czakó, Barbara (2008-09-15), "p-Tolylsulfonylmethyl Isocyanide", Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, Ltd, doi:10.1002/047084289x.rt150.pub2, ISBN 978-0471936237