Di-tert-butyl dicarbonate

• Catalog No.: A14708
• CAS Number: 24424-99-5
• M. F.: C10H18O5
• M. W.: 218.24692
• Purity: 97+%

SYNONYMS

• Title: 二碳酸二叔丁酯
• IUPAC name: di-tert-butyl dicarbonate
• IUPAC Traditional name: di-tert-butyl dicarbonate
• Synonyms: Di-tert-butyl pyrocarbonate; BOC anhydride

DATABASE IDS

• MDL Number: MFCD00008805
• CAS Number: 24424-99-5
• Beilstein Number: 1911173
• EC Number: 246-240-1

PROPERTIES

• Purity: 97+%
• Boiling Point: 56-57°C/0.5mm
• Density: 0.950
• Flash Point: 37°C(99°F)
• Melting Point: 21-24°C
• Refractive Index: 1.4090
• GHS Hazard statements: H330-H315-H317-H335-H318-H228
• European Hazard Symbols: Highly toxic (T+)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P280-P305+P351+P338-P302+P352-P304+P340-P310
• Risk Statements: 11-26-37/38-41-43
• RTECS: HT0230000
• Safety Statements: 9-26-28-36/37/39-45-60
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN2930
• Packing Group: I

REFERENCES

• Carboxylic acids have also been converted to Boc-protected amines, via a one-pot Curtius rearrangement, using the reagent in the presence of sodium azide, with catalytic amounts of TBAB and zinc triflate: Org. Lett., 7, 4107 (2005).
• Reagent for amino group protection as the tert-butyl carbamate (tert-butoxycarbonyl, Boc derivatives), in high yield under mild conditions, widely used in peptide chemistry; see Appendix 6. For practical details, literature references and tabulated results, see: Org. Synth. Coll., 7, 70 (1990). For further examples see: Synthesis, 223 (1987): Org. Synth.Coll., 9, 124, 300 (1998). Benzyl carbamates (Cbz, Z) may be transformed into Boc in a one pot procedure catalyzed by Pd/C: Tetrahedron Lett., 33, 3167 (1992).
• Rapid and efficient formation of Boc derivatives of amines, catayzed by Copper(II) tetrafluoroborate hexahydrate, 26127 has been described: Tetrahdron Lett., 47, 1087 (2006).
• For Boc protection of phenols, alcohols, thiols etc. under phase-transfer conditions, see: Can. J. Chem., 63, 153 (1985).
• Amides can be protected in the presence of a catalytic quantity of DMAP (4-(Dimethylamino)pyridine, A13016): J. Org. Chem., 48, 2424 (1983); Acta Chem. Scand. B, 40, 745 (1986); the amide link of the product undergoes facile alkaline hydrolysis or methanolysis. The nitrogen function of indoles and pyrroles can also be protected under similar conditions: J. Chem. Soc., Chem. Commun., 1699 (1984); Org. Synth.Coll., 9, 121 (1998). 1-Boc indoles may be synthesized from N-Boc 2-alkylanilines: Synthesis, 871 (1991).
• The Boc group is readily cleaved with acid, most often Trifluoroacetic acid, L06374.
• In the presence of 1 equivalent of DMAP in acetonitrile, arylamines are converted to isocyanates, generally in high yield; the dicarbonate here behaves as a convenient phosgene replacement: Angew. Chem. Int. Ed., 34, 2497 (1995). The same reagent system has also been applied to nitroalkanes for the ambient temperature generation of nitrile oxides which were trapped in situ with dipolarophiles: Synthesis, 309 (1997). Carboxylic acids can be esterified in the presence of a catalytic amount of DMAP: Synlett, 263 (2004).
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 1995 (2001).