:TosMIC

{{chembox

| Watchedfields = changed

| verifiedrevid = 443634801

| Reference=[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/188204 p-Toluenesulfonylmethyl isocyanide] at Sigma-Aldrich

| ImageFile1 = TosMIC-2D-skeletal.png

| ImageFile2 = TosMIC-from-xtal-3D-bs-17.png

| PIN=1-(Isocyanomethanesulfonyl)-4-methylbenzene

| OtherNames=Toluenesulfonylmethyl isocyanide

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=36635-61-7

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 142204

| EINECS = 36635-61-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = C35FD6OLH8

| PubChem=161915

| InChI = 1/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3

| InChIKey = CFOAUYCPAUGDFF-UHFFFAOYAC

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = CFOAUYCPAUGDFF-UHFFFAOYSA-N

| SMILES = O=S(=O)(c1ccc(cc1)C)C[N+]#[C-]

}}

|Section2={{Chembox Properties

| C=9|H=9|N=1|O=2|S=1

| Appearance=

| Density=

| MeltingPtC=109 to 113

| Solubility=

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|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

| GHSPictograms = {{GHS06}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|301|311|331}}

| PPhrases = {{P-phrases|261|264|270|271|280|301+310|302+352|304+340|311|312|321|322|330|361|363|403+233|405|501}}

}}

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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 to convert ketones to nitriles (Van Leusen reaction) and in the preparation of oxazoles.{{Cite journal|last1=Keeri|first1=Abdul Raheem|last2=Gualandi|first2=Andrea|last3=Mazzanti|first3=Andrea|last4=Lewinski|first4=Janusz|last5=Cozzi|first5=Pier Giorgio|date=2015-12-21|title=Me2Zn-Mediated Catalytic Enantio- and Diastereoselective Addition of TosMIC to Ketones|journal=Chemistry – A European Journal|language=en|volume=21|issue=52|pages=18949–18952|doi=10.1002/chem.201504362|pmid=26549317|issn=1521-3765}} and imidazoles.{{ OrgSynth |author1=Hoogenboom, B. E.|author2=Oldenziel, O. H.|author3=van Leusen, A. M. | title = p-Tolylsulfonylmethyl Isocyanide | volume = 57 | pages = 102 | year = 1977 | doi = 10.15227/orgsyn.057.0102 }} The versatility of TosMIC in organic synthesis has been documented.{{Cite web|url=https://www.organic-chemistry.org/Highlights/2005/05May.shtm|title=Toluenesulphonylmethyl isocyanide (TOSMIC) and the van Leusen MCR|website=www.organic-chemistry.org|access-date=2017-02-28}} 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.{{Citation|last1=van Leusen|first1=Albert M.|title=p-Tolylsulfonylmethyl Isocyanide|date=2008-09-15|encyclopedia=Encyclopedia of Reagents for Organic Synthesis|publisher=John Wiley & Sons, Ltd|language=en|doi=10.1002/047084289x.rt150.pub2|isbn=978-0471936237|last2=van Leusen|first2=Daan|last3=Czakó|first3=Barbara}}