10353. Di-tert-Butyl Dicarbonate

Nomenclature

CAS number: 24424-99-5
Dicarbonic acid C,C′-bis(1,1-dimethylethyl) ester; di-tert-butyl oxydiformate; di-tert-butyl pyrocarbonate; Boc anhydride; Boc2O.
C10H18O5; mol wt 218.25.
C 55.03%, H 8.31%, O 36.65%.

Description and references

Reagent used to introduce the tert-butoxycarbonyl (Boc) group to protect amines, often in peptide synthesis. Also used in the protection of alcohols and other functionalities. Prepn: J. H. Howe, L. R. Morris, J. Org. Chem. 27, 1901 (1962) DOI; B. M. Pope et al., Org. Synth. coll. vol. VI, 418 (1988). Functional group protection: D. S. Tarbell et al., Proc. Natl. Acad. Sci. USA 69, 730 (1972) DOI PubMed; E. Ponnusamy et al., Synthesis 1986, 48 DOI; Y. Basel, A. Hassner, J. Org. Chem. 65, 6368 (2000) DOI PubMed. Review: M. Wakselman in Encyclopedia of Reagents for Organic Synthesis 3, L. A. Paquette, Ed. (Wiley, New York, 1995) pp 1602-1608.

Chemical structure

Properties

Colorless liquid. bp0.5 56-57°; bp0.3 50-51°. mp 21-22°. nD25 1.4078. Poisonous. Flammable. Irritant. Flash pt, closed cup: 98.6°F (37°C). Sol in most organic solvents. Insol in cold water. Store at 2-8°C in absence of moisture.

Use

Reagent in synthetic organic chemistry.