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205249

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

Application

Reagent for the preparation of Boc protected amines.
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.
Reagent for the introduction of the Boc protecting group.
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)
Protection of alcohols as Boc derivatives via Lewis acid catalysis.

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

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
BCCL9400
MKCZ9024
BCCP3138
BCCH9765
MKCZ6627

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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
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
Synthetic Communications, 23, 1443-1443 (1993)
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