Phenyl(trichloromethyl)mercury

Abstract

[3294-57-3] C7H5Cl3Hg (MW 396.06) InChI = 1S/C6H5.CCl3.Hg/c1-2-4-6-5-3-1;2-1(3)4;/h1-5H;; InChIKey = MVIAEGXPYBMVPT-UHFFFAOYSA-N (transfers :CCl2 to many unsaturated systems, to heteroatoms, and to several σ-bonds) Physical Data: mp 117–118 °C. Solubility: sol ether, benzene, chloroform. Form Supplied in: colorless solid; commercially available. Preparative Methods: prepared from PhHgBr either by reaction with Potassium tert-Butoxide–Chloroform in benzene at 10 °C in 66% yield,2 or by treatment with Sodium Methoxide–Ethyl Trichloroacetate in 62% yield.3 Phenylmercury(II) Chloride furnishes PhHgCCl3 by reaction with Sodium Trichloroacetate in refluxing DME (65%).4 A two-phase approach from PhHgCl and CHCl3 using aqueous Sodium Hydroxide–Potassium Fluoride and small amounts of Benzyltriethylammonium Chloride furnishes PhHgCCl3 in 72% yield.5 Purification: recrystallization from chloroform. Handling, Storage, and Precautions: flame-dried glassware and an atmosphere of dry nitrogen are used for the reactions. Organomercury(II) compounds should be carefully handled and skin contact and inhalation should be particularly avoided. All reactions must be conducted in a well-ventilated fume hood. The reagent is light sensitive and should be stored under nitrogen at 4 °C.