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205249

Sigma-Aldrich

Di-tert-butyl dicarbonate

ReagentPlus®, 99%

Synonym(s):
Di-tert-butyl pyrocarbonate, Boc anhydride
Linear Formula:
[(CH3)3COCO]2O
CAS Number:
Molecular Weight:
218.25
Beilstein:
1911173
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

product line

ReagentPlus®

assay

99%

application(s)

peptide synthesis: suitable

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.)

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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Packaging

10, 50, 100 g in poly bottle
10 kg in composite drum
1 kg in poly bottle

Application

Protection of alcohols as Boc derivatives via Lewis acid catalysis.
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.
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 preparation of Boc protected amines.

Warning

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

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

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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 Code

3 - Flammable liquids

WGK Germany

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

Certificate of Analysis

Certificate of Origin

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)
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...

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