Lithium 2-Lithiobenzenethiolate

[117526-82-6] C6H4SLi2 (MW 122.05) InChI = 1S/C6H5S.2Li/c7-6-4-2-1-3-5-6;;/h1-4,7H;;/q;;+1/p-1 InChIKey = APWYCTQUEYBITB-UHFFFAOYSA-M (reagent for preparation of ortho-substituted thiophenols1) Preparative Methods: easily prepared in the form of a white viscous slurry by stirring Thiophenol with 2 equiv n‐Butyllithium and 2 equiv N,N,N′,N′‐Tetramethylethylenediamine in dry cyclohexane in a nitrogen atmosphere for 20 h.1 No purification of the crude product is generally required. It is stable in the absence of air and moisture. Handling, Storage, and Precautions: the title reagent 1 is best made as needed and should be handled and stored under nitrogen in a fume hood. Both preparation and decomposition of 1 on exposure to moisture release the foul smelling, toxic thiophenol. Great care should be taken in disposing of 1 and cleaning apparatus exposed to 1. Excess thiophenol or reagent 1 should be destroyed in a good fume hood using an oxidizing agent such as sodium hypochlorite solution (see Thiophenol).