Benzyl chloroformate
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| Names | |
|---|---|
| IUPAC names
Benzyloxycarbonyl chloride Benzyl chloroformate | |
| Other names
Z-Chloride | |
| Identifiers | |
501-53-1  | |
| ChemSpider | 9958 |
| Jmol interactive 3D | Image |
| PubChem | 10387 |
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| Properties | |
| C8H7ClO2 | |
| Molar mass | 170.59 g·mol−1 |
| Density | 1.195 g/cm3 |
| Boiling point | 103 °C (217 °F; 376 K) (20 Torr) |
| Hazards | |
| Safety data sheet | External MSDS |
| EU classification (DSD) |
 C N Xn |
| R-phrases | R34, R50/53 |
| S-phrases | (S1/2), S26, S45, S60, S61 |
| Flash point | 80 °C (176 °F; 353 K) |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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.
Preparation
In lab scale by dropping Benzyl alcohol to liquid Phosgene at -20 °C. Phosgene is used in excess to minimise the production of the diester.[1]
Uses
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 are used.
References
- ↑ Carbonate derivatives of methyl α-D-mannopyranoside and of D-mannose L. Hough and J. E. Priddle J. Chem. Soc., 1961, 3178-3181 DOI: 10.1039/JR9610003178