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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%

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

Di-tert-butyl dicarbonate (Boc anhydride) can be used:
  • As a reagent to introduce Boc protecting group for the amine functionalities.
  • To prepare tert-butyl ethers and Boc-alcohols in presence of Lewis acid catalyst.
  • As a carboxylating agent for the preparation of a variety of tert-butyl carboxylates.
  • For the conversion of amines to corresponding isocyanates, carbamates and urea derivatives.
  • As a coupling reagent for anchoring various carboxylic acids to hydroxymethylated resins.
  • To synthesize quinolinones and 2-(pseudo)haloquinolines from 2-alkenylanilines in presence of DMAP as a catalyst.

Reagent for the introduction of the Boc protecting group.

Packaging

5, 25 g in poly bottle

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

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).

Di-tert-butyl dicarbonate as an efficient coupling reagent for the immobilization of carboxylic acid moieties
de los Angeles Laborde M, et al.
Tetrahedron Letters, 49(31), 4624-4625 (2008)
Aqueous MW eco-friendly protocol for amino group protection
Nardi M, et al.
Royal Society of Chemistry Advances, 5(24), 18751-18760 (2015)
An expeditious, high-yielding construction of the food aroma compounds 6-acetyl-1, 2, 3, 4-tetrahydropyridine and 2-acetyl-1-pyrroline
Harrison TJ and Dake GR
The Journal of Organic Chemistry, 70(26), 10872-10874 (2005)
Beyond a Protecting Reagent: DMAP-Catalyzed Cyclization of Boc-Anhydride with 2-Alkenylanilines
Huang Y-N, et al.
The Journal of Organic Chemistry, 81(11), 4645-4653 (2016)
Di-tert-butyl dicarbonate: a versatile carboxylating reagent
Augustine JK, et al.
Tetrahedron, 65(1), 134-138 (2009)

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