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Benzyl chloroformate

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Benzyl chloroformate Basic information
Benzyl chloroformate Chemical Properties
  • Melting point:-20 °C
  • Boiling point:103 °C20 mm Hg(lit.)
  • Density 1.212 g/mL at 20 °C
  • vapor density 1 (vs air)
  • vapor pressure 1.39 psi ( 20 °C)
  • refractive index n20/D 1.519(lit.)
  • Flash point:197 °F
  • storage temp. 2-8°C
  • solubility Miscible with ether, acetone and benzene.
  • form Solution
  • color Clear slightly yellow to slightly pink
  • OdorIrritating; sharp, penetrating.
  • Water Solubility decomposes
  • Sensitive Moisture Sensitive
  • Merck 14,1801
  • Stability:Stable. Incompatible with water, oxidizing agents. Combustible.
  • CAS DataBase Reference501-53-1(CAS DataBase Reference)
  • NIST Chemistry ReferenceBenzyl chloroformate(501-53-1)
  • EPA Substance Registry SystemCarbonochloridic acid, phenylmethyl ester (501-53-1)
Safety Information
Benzyl chloroformate Usage And Synthesis
  • Chemical Propertieslight yellow liquid
  • UsesIn peptide synthesis to block the amino group.
  • General DescriptionA colorless liquid with an acrid odor. Vapors irritate eyes and mucous membranes. Corrosive to metals and tissue. Long-term inhalation of low concentrations or short-term inhalation of high concentrations can result in adverse health effects.
  • Air & Water ReactionsDecomposes in moist air. Decomposes slowly in water to give corrosive hydrochloric acid and organic acids.
  • Reactivity ProfileBenzyl chloroformate decomposes slowly in water forming benzyl alcohol, HCl, and CO2. Gives off HCl fumes in moist air. Reacts with bases, both organic and inorganic. Attacks many metals especially in humid atmosphere [Handling Chemicals Safely 1980. p. 476]. Catalytic impurity incidents involving the iron catalyzed decomposition of benzoyl chloroformate have caused several explosions. The iron presumably comes from corrosion of steel storage tanks [Loss Prev. Bull., 1975, (003), 2]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].
  • HazardHighly toxic, emits very toxic phosgene fumes at 100C. Irritant to eyes.
  • Health HazardInhalation causes mucous membrane irritation. Eyes are irritated by excessive exposure to vapor. Liquid causes severe irritation of eyes and irritates skin. Ingestion causes irritation of mouth and stomach.
  • Chemical ReactivityReactivity with Water Forms hydrogen chloride (hydrochloric acid). Reaction not very vigorous in cold water; Reactivity with Common Materials: Slow corrosion of metals; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Flush with and rinse with sodium bicarbonate or lime solution; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
  • Safety ProfilePoison by ingestion andinhalation routes. A powerful corrosive irritant. Thermallyunstable. Will react with water or steam to produce toxicand corrosive fumes and heat. Iron salts catalyze theexplosive decomposition of the ester. When heated todecomp
  • Purification MethodsThe commercial material is usually better than 95% pure and may contain some toluene, benzyl alcohol, benzyl chloride and HCl. After long storage (e.g. two years at 4o, Greenstein and Winitz [The Chemistry of the Amino Acids Vol 2 p. 890, J Wiley and Sons NY, 1961] recommended that the liquid should be flushed with a stream of dry air, filtered and stored over sodium sulfate to remove CO2 and HCl which are formed by decomposition. It may further be distilled from an oil bath at a temperature below 85o because Thiel and Dent [Annalen 301 257 1898] stated that benzyloxycarbonyl chloride decarboxylates to benzyl chloride slowly at 100o and vigorously at 155o. Redistillation at higher vacuum below 85o yields material which shows no other peaks than those of benzyloxycarbonyl chloride by NMR spectroscopy. [Beilstein 6 IV 2278.] LACHRYMATORY and TOXIC.
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