Benzyl chloroformate
Benzyl chloroformate, also known as benzyl chlorocarbonate or Z-chloride, is the benzyl ester of chloroformic acid. It can be also described as the chloride of the benzyloxycarbonyl (Cbz or Z) group. In its pure form it is a water-sensitive oily colorless liquid, although impure samples usually appear yellow. It possesses a characteristic pungent odor and degrades in contact with water.
| Names | |
|---|---|
| Preferred IUPAC name
Benzyl carbonochloridate | |
| Other names
Benzyl chloroformate Benzyloxycarbonyl chloride Z-Chloride | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.007.205 |
| EC Number |
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PubChem CID |
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| RTECS number |
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| UNII | |
| UN number | 1739 |
CompTox Dashboard (EPA) |
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SMILES
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| Properties | |
| C8H7ClO2 | |
| Molar mass | 170.59 g·mol−1 |
| Appearance | colorless liquid, may appear yellow due to impurities |
| Odor | pungent |
| Density | 1.195 g/cm3 |
| Boiling point | 103 °C (217 °F; 376 K) (20 Torr) |
| degrades | |
Refractive index (nD) |
1.519 (589 nm) |
| Hazards | |
| GHS labelling: | |
| Danger | |
| H314, H410 | |
| P260, P264, P273, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P391, P405, P501 | |
| Flash point | 80 °C (176 °F; 353 K) |
| Safety data sheet (SDS) | External MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
The compound was first prepared by Leonidas Zervas in the early 1930s who used it for the introduction of the benzyloxycarbonyl protecting group, which became the basis of the Bergmann-Zervas carboxybenzyl method of peptide synthesis he developed with Max Bergmann. This was the first successful method of controlled peptide chemical synthesis and for twenty years it was the dominant procedure used worldwide until the 1950s. To this day, benzyl chloroformate is often used for amine group protection.