Skip to Content
MilliporeSigma
All Photos(1)

Documents

361941

Sigma-Aldrich

Di-tert-butyl dicarbonate

≥99%, for peptide synthesis, ReagentPlus®

Synonym(s):

Boc anhydride, Di-tert-butyl pyrocarbonate

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
[(CH3)3COCO]2O
CAS Number:
24424-99-5
Molecular Weight:
218.25
Beilstein/REAXYS Number:
1911173
EC Number:
246-240-1
MDL number:
MFCD00008805
UNSPSC Code:
12352302
PubChem Substance ID:
24862282
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

Looking for similar products? Visit Product Comparison Guide

Application

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)
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.

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

signalword

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

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

98.6 °F - closed cup

flash_point_c

37 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service