Chemical Properties
clear colorless to almost colorless liquid
Physical properties
mp 14–15 °C; bp 55–56 °C/10 mmHg; d 0.909 g cm?3.
Uses
Silylating reagent for the protection of 1? and 2? alcohols
and N-silylation of amines and amides; used in the preparation
of thexyldimethylsilyl triflate; formation of α-silyl hydrazones;
formylation of polyfluoroalkyl halides.
Thexyldimethylsilyl chloride (TDS-Cl) was first introduced as a more
easily prepared alternative to the more commonly used t-butyldimethylsilyl chloride for the protection of alcohols.
Uses
Protecting reagent for alcohols and other functional groups. Employed in the synthesis of silicon naphthocyanine and cyclodextrin derivatives, which are useful as antitumor dyes and chiral stationary phases, respectively.
Preparation
To a mixture of dimethylchlorosilane
(10 mL, 92 mmol) and AlCl3 (0.680 g, 5 mmol) at 25°Cwas
added 2,3-dimethyl-2-butene (11 mL, 91 mmol). After stirring
for 4 h at ambient temperature, the mixture was filtered and
distilled to yield 15.2 g of TDS-Cl (93%).
Purification Methods
Purify it by fractional distillation and store it in small aliquots in sealed ampoules. It is very sensitive to moisture and is estimated by dissolving an aliquot in excess of 0.1M NaOH and titrating with 0.1M HCl using methyl red as indicator [Szabó et al. Helv Chim Acta 67 2128 1984].
