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34660 Sigma-Aldrich

Di-tert-butyl dicarbonate

≥98.0% (GC)

Synonym: Boc anhydride, Boc2O, 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 329755051

  •  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
assay   ≥98.0% (GC)
application(s)   peptide synthesis: suitable
refractive index   n20/D 1.409 (lit.)
bp   56-57 °C/0.5 mmHg (lit.)
mp   23 °C (lit.)
  23 °C
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

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) can 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.

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.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN 2929 3(6.1) / PGII
WGK Germany 
WGK 3
RTECS 
HT0230000
Flash Point(F) 
98.6 °F
Flash Point(C) 
37 °C
Protocols & Articles
Peer-Reviewed Papers
15

References

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