Density 1.2 g/cm³ Boiling point 103 °C | Formula C8H7ClO2 Melting point 0 °C | |
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Benzyl chloroformate is the benzyl ester of chloroformic acid. It is also known as benzyl chlorocarbonate and is an oily liquid whose color is anywhere from yellow to colorless. It is also known for its pungent odor. When heated, benzyl chloroformate decomposes into phosgene and if it comes in contact with water it produces toxic, corrosive fumes.
Contents
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Preparation
It is prepared in the lab by dropping benzyl alcohol into liquid phosgene at −20 °C. Phosgene is used in excess to minimise the production of the carbonate.
Uses
Benzyl chloroformate is used in organic synthesis for the introduction of the carboxybenzyl (abbreviated Cbz or Z) protecting group for amines:
The newly formed Cbz protecting group can be removed under reductive conditions. Typically hydrogen gas and activated palladium on carbon are used.