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

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

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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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)

Warning

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

Legal Information

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

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

205249-1KG:
205249-50G:
205249-25KG:
205249-CH:
205249-15KG:
205249-10G:
205249-VAR:
205249-10KG:
205249-100G:
205249-BULK:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Synthetic Communications, 23, 1443-1443 (1993)
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
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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