| Benzyl chloroformate | |
|---|---|
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Benzyloxycarbonyl chloride |
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| Identifiers | |
| CAS number | 501-53-1 |
| PubChem | 10387 |
| ChemSpider | 9958 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C8H7ClO2 |
| Molar mass | 170.59 g mol−1 |
| Density | 1.195 g/cm3 |
| Melting point |
0 °C |
| Boiling point |
103 °C (20 Torr) |
| Hazards | |
| MSDS | External MSDS |
| EU Index | 607-064-00-4 |
| EU classification | C N Xn |
| R-phrases | R34, R50/53 |
| S-phrases | (S1/2), S26, S45, S60, S61 |
| Flash point | 80 °C |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
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.
Benzyl chloroformate is used in organic synthesis for the introduction of the carboxybenzyl (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 is used.