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SIMes (or HImes) is an N-heterocyclic carbene. It is a white solid that dissolves in organic solvents. The compound is used as a ligand in organometallic chemistry. It is structurally related to the more common ligand IMes but with a saturated backbone (the S of SIMes indicates a saturated backbone). It is slightly more flexible and is a component in Grubbs II. It is prepared by alkylation of trimethylaniline by dibromoethane followed by ring closure and dehydrohalogenation.