Benzyl chloroformate

Benzyl chloroformate
Skeletal formula of benzyl chloroformate
Ball-and-stick model of the benzyl chloroformate molecule
Names
Preferred IUPAC name
Benzyl carbonochloridate
Other names
Benzyl chloroformate
Benzyloxycarbonyl chloride
Z-Chloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.205 Edit this at Wikidata
EC Number
  • 207-925-0
RTECS number
  • LQ5860000
UNII
UN number 1739
  • InChI=1S/C8H7ClO2/c9-8(10)11-6-7-4-2-1-3-5-7/h1-5H,6H2 checkY
    Key: HSDAJNMJOMSNEV-UHFFFAOYSA-N checkY
  • InChI=1/C8H7ClO2/c9-8(10)11-6-7-4-2-1-3-5-7/h1-5H,6H2
    Key: HSDAJNMJOMSNEV-UHFFFAOYAW
  • ClC(=O)OCc1ccccc1
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
1.519 (589 nm)
Hazards
GHS labelling:
GHS06: ToxicGHS09: Environmental hazard
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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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.

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.

  1. ^ a b Katsoyannis, P. G., ed. (1973). The Chemistry of Polypeptides. New York: Plenum Press. doi:10.1007/978-1-4613-4571-8. ISBN 978-1-4613-4571-8. S2CID 35144893. Archived from the original on 2022-10-13. Retrieved 2021-04-01.
  2. ^ Bergmann, Max; Zervas, Leonidas (1932). "Über ein allgemeines Verfahren der Peptid-Synthese" [On a general method of peptide synthesis]. Berichte der deutschen chemischen Gesellschaft. 65 (7): 1192–1201. doi:10.1002/cber.19320650722.