TosMIC

TosMIC^[1]

Names

IUPAC name

1-(isocyanomethylsulfonyl)-4-methylbenzene

Identifiers

CAS Number

36635-61-7^Y

3D model (JSmol)

Interactive image

ChemSpider

142204^Y

ECHA InfoCard

100.048.293

PubChem CID

161915

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

R-phrases (outdated)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S-phrases (outdated)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).

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Infobox references

Toluenesulfonylmethyl isocyanide or TOSMIC 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]

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. ISSN 1521-3765. doi:10.1002/chem.201504362.
↑ Hoogenboom, B. E.; Oldenziel, O. H.; van Leusen, A. M. (1977). "p-TOLYLSULFONYLMETHYL ISOCYANIDE". Org. Synth. 57: 102. ; Coll. Vol., 6, p. 987
↑ "Toluenesulphonylmethyl isocyanide (TOSMIC) and the van Leusen MCR". www.organic-chemistry.org. Retrieved 2017-02-28.

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