Di-tert-butyl dicarbonate

Di-tert-butyl dicarbonate
Names
Preferred IUPAC name
Di-tert-butyl dicarbonate
Other names
Di-t-butyl pyrocarbonate
Boc anhydride
Boc2O
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.042.021 Edit this at Wikidata
EC Number
  • 246-240-1
UNII
  • InChI=1S/C10H18O5/c1-9(2,3)14-7(11)13-8(12)15-10(4,5)6/h1-6H3 checkY
    Key: DYHSDKLCOJIUFX-UHFFFAOYSA-N checkY
  • InChI=1/C10H18O5/c1-9(2,3)14-7(11)13-8(12)15-10(4,5)6/h1-6H3
    Key: DYHSDKLCOJIUFX-UHFFFAOYAG
  • O=C(OC(=O)OC(C)(C)C)OC(C)(C)C
Properties
C10H18O5
Molar mass 218.249 g·mol−1
Appearance Colorless solid or oil
Density 0.95 g·cm−3
Melting point 22 to 24 °C (72 to 75 °F; 295 to 297 K)
Boiling point 56 to 57 °C (133 to 135 °F; 329 to 330 K) (0.5 mmHg)
Insoluble
Solubility in other solvents Soluble in most organic solvents
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Very toxic on inhalation T+, LC50 = 100 mg/m3 (4 hr, rat)
Related compounds
Related compounds
 Ethyl chloroformate
Phosgene
Diethyl pyrocarbonate
Dimethyl dicarbonate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Di-tert-butyl dicarbonate is a reagent widely used in organic synthesis.[1] Since this compound can be regarded formally as the acid anhydride derived from a tert-butoxycarbonyl (Boc) group, it is commonly referred to as Boc anhydride. This pyrocarbonate reacts with amines to give N-tert-butoxycarbonyl or so-called Boc derivatives. These carbamate derivatives do not behave as amines, which allows certain subsequent transformations to occur that would be incompatible with the amine functional group. The Boc group can later be removed from the amine using moderately strong acids (e.g., trifluoroacetic acid). Thus, Boc serves as a protective group, for instance in solid phase peptide synthesis. Boc-protected amines are unreactive to most bases and nucleophiles, allowing for the use of the fluorenylmethyloxycarbonyl group (Fmoc) as an orthogonal protecting group.

  1. ^ M. Wakselman, "Di-t-butyl Dicarbonate" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289X.