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Di-tert-butyl dicarbonate

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Di-tert-butyl dicarbonate Basic information
Di-tert-butyl dicarbonate Chemical Properties
  • Melting point:23 °C(lit.)
  • Boiling point:65-67 °C
  • Density 0.95 g/mL at 25 °C(lit.)
  • refractive index n20/D 1.409(lit.)
  • Flash point:99 °F
  • storage temp. 2-8°C
  • form Low Melting Crystalline Solid
  • color White
  • Specific Gravity0.950
  • Water Solubility Miscible with decalin, toluene, carbon tetrachloride, tetrahydrofuran, dioxane, alcohols, acetone, acetonitrile and dimethylformamide. Immiscible with water.
  • Sensitive Moisture Sensitive
  • BRN 1911173
  • InChIKeyDYHSDKLCOJIUFX-UHFFFAOYSA-N
  • CAS DataBase Reference24424-99-5(CAS DataBase Reference)
  • EPA Substance Registry SystemDicarbonic acid, bis(1,1-dimethylethyl) ester (24424-99-5)
Safety Information
MSDS
Di-tert-butyl dicarbonate Usage And Synthesis
  • Chemical PropertiesWhite to off-white microcrystalline powder
  • Chemical PropertiesDi-tert-butyl dicarbonate (Boc2O) and di-tert-butyl tricarbonate ((BocO)2CO)  have been used as amine carbonylating reagents to obtain linear or branched aliphatic isocyanates.
    most of the known methods for transforming amines into isocyanates are not mild enough and furnish undefined products as a result of uncontrolled side reactions. However, 4-dimethylaminopyridine (DMAP)-catalyzed reaction with activated carbonates as C1 building blocks constitutes a convenient laboratory method for the phosgene-free isocyanation of amines. A procedure has been described whereby alkyl- and arylamines are converted into isocyanates in high yields by reaction with activated carbonates (for example, di-tert-butyl dicarbonate, Boc2O) in the presence of a catalytic amount of a nucleophilic nitrogen base at room temperature.
    Di-tert-butyl dicarbonate (Boc2O) is a widely used reagent for introducing protecting groups in peptide synthesis. The reaction of substituted anilines with Boc2O in the presence of a stoichiometric amount of 4-dimethylaminopyridine (DMAP) in an inert solvent (acetonitrile, dichloromethane, ethyl acetate, tetrahydrofuran, toluene) at room temperature leads to aryl isocyanates in almost quantitative yields within 10 min.
  • UsesReagent commonly used in organic chemistry for the introduction of the BOC protecting group.
  • Usesreagent for t-BOC-protected amines
  • UsesReagent for the preparation of Boc-amino acids and peptides in high yields.
  • Purification MethodsMelt the ester by heating at ~35o, and distil it in a vacuum. If IR and NMR ( 1810m 1765 cm-1 , in CCl4 1.50 singlet) suggest very max impure, then wash with an equal volume of H2O containing citric acid to make the aqueous layer slightly acidic, collect the organic layer and dry it over anhydrous MgSO4 and distil it in a vacuum. [Pope et al. Org Synth 57 45 1977, Keller et al. Org Synth 63 160 1985, Grehn et al. Angew Chem 97 519 1985.] FLAMMABLE.
Di-tert-butyl dicarbonate Preparation Products And Raw materials
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