Abstract
[[173035-11-5], C21H26N2 (MW 306.44) InChI = 1S/C21H26N2/c1-14-9-16(3)20(17(4)10-14)22-7-8-23(13-22)21-18(5)11-15(2)12-19(21)6/h9-12H,7-8H2,1-6H3 InChIKey = LSMWOQFDLBIYPM-UHFFFAOYSA-N Alternate Name: SIMes. Physical Data: mp = 107–109 °C (hexane).1 Solubility: soluble in THF, benzene, and toluene; insoluble in pentane and hexane; reacts with chlorinated solvents, alcohols, acetone, and acetonitrile. Form Supplied in: white crystalline solid, crystal structure available.1 Analysis of Reagent Purity: 1H and 13C NMR spectroscopies. Preparative Methods: 1,3-Dimesityl-4,5-dihydroimidazol-2-ylidene can be synthesized following several procedures; the most widely used being the deprotonation of the corresponding imidazolinium salt by a strong base (typically, sodium hydride, potassium hydride, potassium tert-butoxide, sodium tert-butoxide, DBU, etc). Formation of free N-heterocyclic carbenes can also be carried out by elimination of methanol or chloroform from the corresponding adducts at high temperature under vacuum. Purification: recrystallization from THF/hexane or sublimation. Handling, Storage, and Precautions: store under inert atmosphere (nitrogen or argon). For practical reasons, handling in a dry box is advised. Decomposes on exposure to water and is susceptible to oxidative decomposition.
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