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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

Certificate of Origin

Exhaustive tert-Butoxycarbonylation of Peptide Nitrogens
L. Grehn and Ragnarsson U
Angewandte Chemie (International Edition in English), 24(6), 510-511 (1985)
Synthesis of chiral oxazolidin-2-ones and imidazolidin-2-ones via DMAP-catalyzed isocyanation of amines with di-tert-butyl dicarbonate
Knolker H-J and Braxmeier T
Tetrahedron Letters, 39(51), 9407-9410 (1998)
Pd-catalyzed decarbonylative Heck olefination of aromatic carboxylic acids activated in situ with di-tert-butyl dicarbonate
Goossen LJ, et al.
Synlett, 2002(10), 1721-1723 (2002)
A mild two-step method for the hydrolysis of lactams and secondary amides
D.L. Flynn et al.
The Journal of Organic Chemistry, 48(14), 2424-2426 (1983)
A new efficient synthesis of isothiocyanates from amines using di-tert-butyl dicarbonate
Munch H, et al.
Tetrahedron Letters, 49(19), 3117-3119 (2008)

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