p-Tolylsulfonylmethyl Isocyanide

[36635-61-7] C9H9NO2S (MW 195.26) InChI = 1S/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3 InChIKey = CFOAUYCPAUGDFF-UHFFFAOYSA-N (reductive cyanation of ketones2a and aldehydes;2b synthesis of azoles (pyrroles, oxazoles, imidazoles, thiazoles, etc.) by delivering a CNC fragment to polarized double bonds;3 connective reagent for coupling of alkyl halides (or carbonyl compounds) by a CO4a or a CH2 bridge;4b preparation of (formal) Knoevenagel condensation products from aldehydes and ketones5) Alternate Name: tosylmethyl isocyanide; TosMIC. Physical Data: mp 116–117 °C (dec). Solubility: sol THF, CH2Cl2, CHCl3, DME, AcOEt, benzene; slightly sol Et2O, EtOH, MeOH. Form Supplied in: white to near-white, odorless, commercially available solid. Analysis of Reagent Purity: IR (Nujol) 2150 (NC), 1320, 1155 cm−1 (SO2); 1H NMR (CDCl3) δ 2.5 (s, CH3), 4.6 (s, CH2); 13C NMR (CDCl3) δ 61.1 (CH2), 165.7 (NC). Preparative Method: by dehydration of N-(p-tolylsulfonylmethyl)formamide.6 Handling, Storage, and Precautions: shelf stable.