Benzyl chloroformate
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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 | |
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Preferred IUPAC name
Benzyl carbonochloridate | |
Other names
Benzyl chloroformate Benzyloxycarbonyl chloride Z-Chloride | |
Identifiers | |
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3D model (JSmol) |
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ChemSpider |
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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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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).
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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.[1][2] 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.[1] To this day, benzyl chloroformate is often used for amine group protection.