Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
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.
^ abKatsoyannis, 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.
^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.
and 27 Related for: Benzyl chloroformate information
Benzylchloroformate, also known as benzyl chlorocarbonate or Z-chloride, is the benzyl ester of chloroformic acid. It can be also described as the chloride...
methyl chloroformate, which is commercially available. Chloroformates are used as reagents in organic chemistry. For example, benzylchloroformate is used...
Important chloroformate esters include 4-nitrophenyl chloroformate, fluorenylmethyloxycarbonylchloride, benzylchloroformate and ethyl chloroformate. Chloroacetic...
IUPAC nomenclature, the prefix benzyl refers to a C6H5CH2 substituent, for example benzyl chloride or benzyl benzoate. Benzyl is not to be confused with phenyl...
ester of carbamic acid (O=C(OH)(NH2)) and benzyl alcohol, although it is produced from benzylchloroformate with ammonia. It is a white solid that is...
Leonidas Zervas in the early 1930s and usually added via reaction with benzylchloroformate. It is removed under harsh conditions using HBr in acetic acid, or...
hydrogen chloride side-product. Phosgene is used to produce chloroformates such as benzylchloroformate: R−OH + COCl2 → R−O−C(=O)−Cl + HCl In these syntheses...
common amine protecting groups, such as BOC, FMOC, benzylchloroformate and trichloroethyl chloroformate are carbamates. Urethane (ethyl carbamate) was once...
reagent in the installation of the carboxybenzyl (Cbz) group using benzylchloroformate in EtOAc for the N-protection of amines and amides. Doping MgO (about...
as an inorganic compound) Chloroformic acid forms chloroformate esters, e.g. methyl chloroformate (Cl−C(=O)−O−CH3) (if one classifies chloroformic acid...
g/mol, exact mass: 170.0135 u) may refer to: Anisoyl chloride Benzylchloroformate, or benzyl chlorocarbonate This set index page lists chemical structure...
Pyridine (1) is reduced with sodium borohydride in presence of benzylchloroformate to the Cbz protected dihydropyridine 2. The asymmetric Diels-Alder...
chloride UN 1737 6.1 Benzyl bromide UN 1738 6.1 Benzyl chloride or Benzyl chloride unstabilized UN 1739 8 Benzylchloroformate UN 1740 8 Hydrogen difluorides...
carboxybenzyl group discovered by Zervas is introduced by reaction with benzylchloroformate, originally in aqueous sodium carbonate solution at 0 °C: The protecting...
acid. The product is treated first with N-methylmorpholine, isobutyl chloroformate, and benzylamine, next with methyl iodide and silver oxide, forming...
a benzyl ester on the carboxyl group, a fluorenylmethylenoxy carbamate on the amine group, and a tert-butyl ether on the phenol group. The benzyl ester...
H2O The diphenoxide (Na2(OC6H4)2CMe2) reacts with phosgene to give a chloroformate, which subsequently is attacked by another phenoxide. The net reaction...
then protected as its ethyl carbamate by acylation with ethyl chloroformate (6). The benzyl carbamate function on nitrogen at the 4 position is next removed...
carbonyls are urea and the carbamates, the derivatives of acyl chlorides chloroformates and phosgene, carbonate esters, thioesters, lactones, lactams, hydroxamates...
were combined in an amine-carbonyl condensation followed by methyl chloroformate quench to triene 3 which was then reacted in a Diels–Alder reaction...
(product) using alkenyl boronic acids and chiral thiourea catalyst: Chloroformates are required as electrophilic activating agents. Also, a 1,2-amino alcohol...
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