TosMIC

TosMIC^[1]
Names
	Preferred IUPAC name 1-(Isocyanomethanesulfonyl)-4-methylbenzene
	Other names Toluenesulfonylmethyl isocyanide
Identifiers
CAS Number	36635-61-7 ;
3D model ( JSmol)	Interactive image;
ChemSpider	142204 ;
ECHA InfoCard	100.048.293
EC Number	36635-61-7;
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
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H331
Precautionary statements	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). verify (what is ?) Infobox references

TosMIC (toluenesulfonylmethyl isocyanide) is an

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
PMID 26549317
.

^ Hoogenboom, B. E.; Oldenziel, O. H.; van Leusen, A. M. (1977). "p-TOLYLSULFONYLMETHYL ISOCYANIDE". Organic Syntheses. 57: 102; Collected Volumes, vol. 6, p. 987.

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

ISBN 978-0471936237

ISBN 0471264180
.

Retrieved from "https://en.wikipedia.org/w/index.php?title=TosMIC&oldid=1195936832"

[1] -Toluenesulfonylmethyl isocyanide at Sigma-Aldrich

[2] PMID 26549317
.

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

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

[5] ISBN 978-0471936237

[6] ISBN 0471264180
.

[1]

[2]

[3]

[4]

[5]

Further reading

References