t-Butyldimethylsilyl Perchlorate

t-BuMe2Si-OClO3

[67124-66-7]  · C6H15ClO4Si  · t-Butyldimethylsilyl Perchlorate  · (MW 214.72)

(silylating reagent)

Form Supplied in: clear liquid.

Preparative Methods: prepared in a one-step trityl salt-silyl hydride exchange reaction between t-butyldimethylsilane and Triphenylmethyl Perchlorate (eq 1).1

Purification: distillation under reduced pressure.1

Handling, Storage, and Precautions: potentially explosive; moisture sensitive; safety shield recommended.

The hindered t-butyldimethylsilyl (TBDMS) group has synthetic utility as a very stable alcohol-protecting group. The advantage of TBDMS perchlorate over the corresponding chloride in the protection of secondary and tertiary alcohols is reflected in the relative rates of silylation (Table 1).1

Although stable, removal of the protecting group with 1% HCl in 95% EtOH at rt is quantitative after 15 min.1


1. Barton, T. J.; Tully, C. R. JOC 1978, 43, 3649.

Roberta Pelletier & James S. Panek

Boston University, MA, USA



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