199133

Sigma-Aldrich

Di-tert-butyl dicarbonate

reagent grade, 97%

Synonym(s):
Di-tert-butyl pyrocarbonate, Boc anhydride
Linear Formula:
[(CH3)3COCO]2O
CAS Number:
Molecular Weight:
218.25
Beilstein/REAXYS Number:
1911173
EC Number:
MDL number:

grade

reagent grade

assay

97%

refractive index

n20/D 1.409 (lit.)

bp

56-57 °C/0.5 mmHg (lit.)

mp

23 °C (lit.)

density

0.95 g/mL at 25 °C (lit.)

SMILES string

CC(C)(C)OC(=O)OC(=O)OC(C)(C)C

InChI

1S/C10H18O5/c1-9(2,3)14-7(11)13-8(12)15-10(4,5)6/h1-6H3

InChI key

DYHSDKLCOJIUFX-UHFFFAOYSA-N

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Application

Reagent for the introduction of the Boc protecting group.

Warning

Hydrolyzes to t-butanol and CO2; causes internal pressure in bottle if exposed to moisture.

Certificate of Analysis

Certificate of Origin

Giuseppe Bartoli et al.
The Journal of organic chemistry, 71(26), 9580-9588 (2006-12-16)
The reaction between alcohols and Boc2O leads to the formation of tert-butyl ethers and/or Boc-alcohols, depending on the nature of the Lewis acid catalyst. Product distribution is mainly tuned by the anionic part of the salt. Perchlorates and triflates, anions...
Debmalya Roy et al.
Magnetic resonance in chemistry : MRC, 42(1), 76-80 (2004-01-28)
The precise estimation of the degree of derivatization of functional groups in polymers is important for determining their macroscopic properties. In this work, the quantitative estimation of the extent of esterification of novolac copolymers with di-tert-butyl dicarbonate was studied. Although...
Jason C Green et al.
Organic letters, 13(20), 5500-5503 (2011-09-21)
Total syntheses of two structures purported as (+)-heliananes were completed in six pots. Spectral comparisons, between the synthetic and natural compounds, revealed a misassignment of the eight-membered ring in the heliananes. The key step in the syntheses of the proposed...
Brandon S Fowler et al.
Journal of the American Chemical Society, 132(9), 2870-2871 (2010-02-18)
We report a fundamentally unique approach to the catalytic kinetic resolution of amine derivatives based on formamide and thioformamide substrates. Readily accessible histidine-containing peptides mediate the kinetic resolutions with as little as 5 mol % catalyst. Selectivity factors (k(rel)) as...
Asit K Chakraborti et al.
Organic & biomolecular chemistry, 4(14), 2769-2771 (2006-07-11)
Perchloric acid adsorbed on silica-gel (HClO4-SiO2) was found to be a new, highly efficient, inexpensive and reusable catalyst for chemoselective N-tert-butoxycarbonylation of amines at room temperature and under solvent-free conditions.

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