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Ethyl isocyanoacetate

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Ethyl isocyanoacetate Basic information
Ethyl isocyanoacetate Chemical Properties
  • Boiling point:194-196 °C (lit.)
  • Density 1.035 g/mL at 25 °C (lit.)
  • refractive index n20/D 1.418(lit.)
  • Flash point:184 °F
  • storage temp. 2-8°C
  • form Liquid
  • color Clear amber to dark brown
  • Water Solubility Miscible with organic solvents. Slightly miscible with water.
  • Sensitive Moisture & Light Sensitive
  • BRN 3588613
  • CAS DataBase Reference2999-46-4(CAS DataBase Reference)
Safety Information
Ethyl isocyanoacetate Usage And Synthesis
  • Chemical PropertiesLight yellow to brom liquid
  • UsesEthyl Isocyanoacetate, is a cyclization synthon used to prepare pyrroles, oxazolines, benzodiazepines, oxazoles and imidazoles. Ethyl isocyanoacetate can be used to prepare pyrroles,1,2 oxazolines, benzodiazepines, oxazoles and imidazoles.
  • Preparationsynthesis of ethyl isocyanoacetate
    A solution containing N-formyl glycine ethyl ester (1, 1.31 g, 10 mmol), DIPEA (2.62 g, 20 mmol) and DMAP (0.45 g, 3 mmol) in dry DCM (10 mL) was loaded in a sample loop and combined with a second stream containing triphosgene (2, 0.98 g, 3.3 mmol) also dissolved in dry DCM (10 mL) at individual channel flow rates of 0.5 mL/min. The combined stream was directed into two linked 10 mL FEP reactor vessels to achieve a 20 minutes residence time at ambient temperature. The output was collect and the solvent was carefully evaporated to 80% of its total volume. The crude material was filtered through silica (5 g) and washed with DCM (2 × 10 mL) to obtain the salt-free product. The desired product 3 was obtained as dark yellow oil after evaporation of the organic phase (1.03 g, 91 % isolated yield, >97% purity by 1H NMR).
Ethyl isocyanoacetate Preparation Products And Raw materials
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