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Sigma-Aldrich

Di-tert-butyl dicarbonate

≥99%, for peptide synthesis, ReagentPlus®

Synonym(s):

Boc anhydride, Di-tert-butyl pyrocarbonate

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About This Item

Linear Formula:
[(CH3)3COCO]2O
CAS Number:
24424-99-5
Molecular Weight:
218.25
Beilstein:
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

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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

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

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’.

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Aqueous MW eco-friendly protocol for amino group protection
Nardi M, et al.
Royal Society of Chemistry Advances, 5(24), 18751-18760 (2015)
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)
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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