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MilliporeSigma

205249

Sigma-Aldrich

Di-tert-butyl dicarbonate

99%, for peptide synthesis, ReagentPlus®

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/REAXYS Number:
1911173
EC Number:
246-240-1
MDL number:
MFCD00008805
UNSPSC Code:
12352302
PubChem Substance ID:
24852315
NACRES:
NA.22

Key Documents

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Product Name

Di-tert-butyl dicarbonate, ReagentPlus®, 99%

Quality Level

200

product line

ReagentPlus®

assay

99%

form

solid or liquid

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.)

application(s)

peptide synthesis

functional group

carbonate

storage temp.

2-8°C

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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Related Categories

Application

Aminomethyl allene was prepared by reaction of Boc propargyl amine with formaldehyde, diisopropylamine and copper bromide as part of a series of Bovine Plasma Amine Oxidase inactivators.
Protection of alcohols as Boc derivatives via Lewis acid catalysis.
Reagent for the introduction of the Boc protecting group.
Reagent for the preparation of Boc protected amines.
Tris-Boc protected hydrazine allows preparation of Fmoc ester in a chromophoric reagent to monitor solid-phase aldehydes.

Automated Boc protection and deprotection can be done using Synple Automated Synthesis Platform (SYNPLE-SC002), Boc protection cartridges ((SYNPLE-B001), (SYNPLE-B002), and Boc deprotection cartridges (SYNPLE-B011)

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

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

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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

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

98.6 °F - closed cup

flash_point_c

37 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH2569
MKCM0414
BCCG7958
BCCG2168
MKCP8965

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Simon K Shannon et al.
The Journal of organic chemistry, 69(14), 4586-4594 (2004-07-03)
A direct method for quantifying solid-phase aldehydes has been developed, using a new reagent, 4-(9-fluorenylmethyloxycarbonyl)phenylhydrazine (FmPH). The FmPH reagent was synthesized in three steps (24% overall yield) from commercially available p-hydrazinobenzoic acid. Resin-bound aldehydes reacted quantitatively with FmPH, in the
Chunhua Qiao et al.
Journal of the American Chemical Society, 126(25), 8038-8045 (2004-06-24)
Propargylic and activated allylic amines are known to inactivate the quinone-dependent plasma amine oxidases, possibly through active-site modification by the alpha,beta-unsaturated aldehyde turnover products. Although homopropargylamine (1-amino-3-butyne, 1) is a nonobvious candidate as a mechanism-based inhibitor, 1 was found to
Synthetic Communications, 23, 1443-1443 (1993)
Synlett, 2104-2104 (2006)
Hans Peter Reisenauer et al.
Angewandte Chemie (International ed. in English), 53(44), 11766-11771 (2014-09-10)
Carbonic acid (H2CO3), an essential molecule of life (e.g., as bicarbonate buffer), has been well characterized in solution and in the solid state, but for a long time, it has eluded its spectral characterization in the gas phase owing to
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