Chloro(4‐methoxyphenyl)dimethylsilane

chemical structure image [2372‐33‐0] C 9 H 13 ClOSi (MW 200.73) InChI = 1S/C9H13ClOSi/c1‐11‐8‐4‐6‐9(7‐5‐8)12(2,3)10/h4‐7H,1‐3H3 InChIKey = RTYNSTRFACIKRL‐UHFFFAOYSA‐N (ambiphile for CSi bond formation, Tamao–Kumada–Fleming oxidation) Alternate Names: p ‐methoxyphenyldimethylchlorosilane, 1‐(chlorodimethylsilyl)‐4‐methoxybenzene, PMPMe 2 SiCl ( PMP : para‐ methoxyphenyl ) Physical Data: b.p. 100 °C/6 mmHg; d 1.172 g cm −3 . 1 Solubility: sol. most organic solvents. Form Supplied in: colorless oil. 1 Analysis of Reagent Purity: 1 H, 13 C, 29 Si NMR. Preparative Methods: readily prepared from the reaction of 4‐(methoxyphenyl)magnesium bromide and dichlorodimethylsilane. In a typical procedure, 4‐bromoanisole is stirred with magnesium turnings in THF. This mixture is added to a solution of dichlorodimethylsilane in diethyl ether at 0 °C; after 24 hours, hexanes are added to the solution and the mixture is filtered to remove precipitate. Evaporation of volatile materials, followed by vacuum distillation (100 °C at 6 mmHg) afforded the product in good yields. 2 Purification: vacuum distillation. Handling, Storage, and Precautions: incompatible with polar protic solvents. Will slowly react with moisture to form the corresponding silanol and HCl; store under nitrogen or argon atmosphere in a dry environment.