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Sigma-Aldrich

Di-tert-butyl dicarbonate

reagent grade, 97%

Synonym(s):

Boc anhydride, Di-tert-butyl pyrocarbonate

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About This Item

Linear Formula:
[(CH3)3COCO]2O
CAS Number:
24424-99-5
Molecular Weight:
218.25
Beilstein:
1911173
EC Number:
246-240-1
MDL number:
MFCD00008805
UNSPSC Code:
12352000

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.

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Eye Dam. 1 - Flam. Liq. 3 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

98.6 °F - closed cup

Flash Point(C)

37 °C - closed cup

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E E Büllesbach et al.
Hoppe-Seyler's Zeitschrift fur physiologische Chemie, 361(5), 723-734 (1980-05-01)
Nepsilon 29, Nepsilon 59-Bis(methylsulfonylethoxycarbonyl)proinsulin was prepared from native beef proinsulin for its possible use in the semisynthesis of preproinsulin. The modification was made possible by first protecting the alpha-amino group of proinsulin either with the tert-butoxycarbonyl group, after reaction with
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
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.
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
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