Merck
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34660

Sigma-Aldrich

Di-tert-butyl dicarbonate

≥98.0% (GC)

Synonym(s):
Di-tert-butyl pyrocarbonate, Boc anhydride, Boc2O
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

assay

≥98.0% (GC)

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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General description

Di-tert-butyl dicarbonate (Boc2O) is a reagent mainly used for the introduction of the Boc protecting group to amine functionalities. It is also used as a dehydrating agent in some organic reactions, particularly with carboxylic acids, certain hydroxyl groups, or with primary nitroalkanes.

Application

Di-tert-butyl dicarbonate (Boc2O) has been used in the synthesis of:
  • An azobenzene amino acid(aa).
  • N-tert-butoxycarbonyl-3,4-methylenedioxymethamphetamine (t-BOC-MDMA) from MDMA.

It can also be used as a reagent:
  • To introduce acid-labile Boc-protecting group in amino acids, peptides, and proteins.        
  • To prepare styrene derivatives by Heck olefination of aromatic carboxylic acids in the presence of a Pd catalyst.        
  • To synthesize oxazolidin-2-ones and imidazolidin-2-ones by isocyanation of 1,2-aminoalcohols and 1,2-diamines using DMAP as a catalyst.       
  • In the preparation of N-tert-butoxycarbonyl-3,4-methylenedioxymethamphetamine (t-Boc-MDMA) from MDMA.
  • For the conversion of amines to corresponding isocyanates, carbamates, and urea derivatives.
  • In the N-BOC-ylation of amides.
  • In the N-BOC-ylation of sensitive compounds under non-aqueous conditions.
Reagent for the introduction of the Boc protecting group.

Packaging

25, 100, 500 g in poly bottle

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Use of Di-tert-butyl-dicarbonate Both as a Protecting and Activating Group in the Synthesis of Dipeptides
Jhaumeer LS, et al.
Synthetic Communications, 37(23), 4191-4197 (2007)
Synthesis and application of an azobenzene amino acid as a light-switchable turn element in polypeptides.
Aemissegger A & Hilvert D.
Nature Protocols, 2(1), 161-161 (2007)
tert-BUTOXYCARBONYLATION OF AMINO ACIDS AND THEIR DERIVATIVES: N-tert-BUTOXYCARBONYL-l-PHENYLALANINE
O. Keller et al.
Organic Syntheses, 63, 160-160 (1985)
Profiling ephedrine prepared from N-methylalanine via the Akabori-Momotani Reaction.
Doddridge A, et al.
Drug Testing and Analysis, 10(3), 548-556 (2018)
Exhaustive tert-Butoxycarbonylation of Peptide Nitrogens
L. Grehn and Ragnarsson U
Angewandte Chemie (International Edition in English), 24(6), 510-511 (1985)

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