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361941 Sigma-Aldrich

Di-tert-butyl dicarbonate

ReagentPlus®, ≥99%

Synonym: Boc anhydride, Di-tert-butyl pyrocarbonate

  • CAS Number 24424-99-5

  • Linear Formula [(CH3)3COCO]2O

  • Molecular Weight 218.25

  •  Beilstein/REAXYS Number 1911173

  •  EC Number 246-240-1

  •  MDL number MFCD00008805

  •  PubChem Substance ID 24862282

  •  NACRES NA.22

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Properties

Related Categories Amine Protection, Chemical Biology, Chemical Synthesis, Other Protecting and Derivatizing Reagents, Peptide Synthesis and Peptide Chemistry,
Quality Level   200
grade   ReagentPlus®
assay   ≥99%
application(s)   peptide synthesis: suitable
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.)
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

Description

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

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Target organs 
Respiratory system
RIDADR 
UN 2929 3(6.1) / PGII
WGK Germany 
WGK 3
RTECS 
HT0230000
Flash Point(F) 
98.6 °F - closed cup
Flash Point(C) 
37 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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