CHLOROTRIBENZYLSILANE

Physical properties

mp 141–142 °C;1,2 a somewhat higher value (143–145 °C) is cited in the Aldrich catalog.

The Uses of CHLOROTRIBENZYLSILANE

Tribenzylchlorosilane is widely used as reagent for alcohol protection.

What are the applications of Application

Chlorotribenzylsilane is a reagent used as a protecting group for alcohols

Preparation

It is prepared by reaction of benzylmagnesium chloride with SiCl4 in ether; separation from mono- and dibenzylated chlorosilane byproducts is then accomplished by fractional distillation (boiling range 300–360 °C/100 mmHg). Other preparations involve the chlorination of tribenzylsilane using Cl2 or an acyl chloride. No yields are reported for any of the above preparative procedures.

Purification Methods

It is recrystallised three times from pet ether (in slender colourless needles, m 141o). It is sparingly soluble in pet ether but is soluble in Et2O. It does not fume in moist air but is decomposed by H2O to give tribenzyl silanol m 106o (from pet ether). [Robinson & Kipping J Chem Soc 93 439 1908, Jenkins & Post J Org Chem 15 556 1950, Beilstein 16 H 906, 16 IV 1498.]