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Di-tert-butyl dicarbonate

Catalog No. A14708 Name Alfa Aesar
CAS Number 24424-99-5 Website
M. F. C10H18O5 Telephone
M. W. 218.24692 Fax
Purity 97+% Email
Storage Chembase ID: 85817

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 Pictograms GHS02
GHS Pictograms GHS05
GHS Pictograms GHS06
GHS Hazard statements H330-H315-H317-H335-H318-H228
European Hazard Symbols Highly toxic Highly toxic (T+)
European Hazard Symbols Flammable 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
Hazard Class 6.1
UN Number UN2930
Packing Group I

DETAILS

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).