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• W4239771738 abstract "[501-53-1] C8H7ClO2 (MW 170.60) InChI = 1S/C8H7ClO2/c9-8(10)11-6-7-4-2-1-3-5-7/h1-5H,6H2 InChIKey = HSDAJNMJOMSNEV-UHFFFAOYSA-N (protecting agent for many functional groups, especially for the N-protection of amino acids;7 activates pyridine rings toward nucleophilic attack;53 reagent for the preparation of other benzyloxycarbonylating agents3) Alternate Name: benzyloxycarbonyl chloride (CbzCl). Physical Data: colorless oily liquid, bp 103 °C/20 mmHg (with slow decarboxylation to benzyl chloride at this temperature); bp 85–87 °C/7 mmHg; mp 0 °C; d (20 °C) 1.195 g cm−3; nD20 1.5190. Form Supplied in: widely available. Preparative Methods: CbzCl can be readily prepared by the reaction of benzyl alcohol and phosgene, either in toluene solution4 or neat.1b,5, 6 Purification of such freshly prepared CbzCl is often not necessary; indeed, ca. 25% residual toluene solvent does not interfere with derivatization reactions.4 Purification: commercial CbzCl is typically better than 95% pure and is often contaminated by benzyl chloride, benzyl alcohol, toluene, and HCl.2, 3 On storage it can undergo a slow HCl-catalyzed decomposition, even at low temperature.1a,3 It has been recommended1b,2 that CbzCl which has been stored for long periods be purified by flushing with a stream of dry air to remove dissolved CO2 and HCl impurities. Filtration and storage over Na2SO4 may be followed by distillation; it is important that low temperatures (oil bath ≤85 °C)1b and high vacuum be used to minimize thermal decomposition.3 Handling, Storage, and Precautions: CbzCl is highly toxic and is a cancer suspect agent; it is a lachrymator with an acrid odor and should be handled with caution in a fume hood." @default.
• W4239771738 created "2022-05-12" @default.
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• W4239771738 date "2001-04-15" @default.
• W4239771738 modified "2023-09-30" @default.
• W4239771738 title "Benzyl Chloroformate" @default.
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• W4239771738 doi "https://doi.org/10.1002/047084289x.rb052" @default.
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