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Merck

34660

Di-tert-butyl dicarbonate

≥98.0% (GC), for peptide synthesis

Synonym(s):

Boc2O, 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
NACRES:
NA.22
PubChem Substance ID:
329755051
UNSPSC Code:
12352108
EC Number:
246-240-1
MDL number:
MFCD00008805
Beilstein/REAXYS Number:
1911173

Product Name

Di-tert-butyl dicarbonate, ≥98.0% (GC)

InChI key

DYHSDKLCOJIUFX-UHFFFAOYSA-N

InChI

1S/C10H18O5/c1-9(2,3)14-7(11)13-8(12)15-10(4,5)6/h1-6H3

SMILES string

CC(C)(C)OC(=O)OC(=O)OC(C)(C)C

assay

≥98.0% (GC)

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

functional group

carbonate

storage temp.

2-8°C

Quality Level

200

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Application

Di-tert-butyl dicarbonate (Boc2O) has been used in the synthesis of:
  • An azobenzene amino acid(aa).
  • N-tert-butoxycarbonyl-3,4-methylenedioxymethamphetamine (t-BOC-MDMA) from MDMA.

It can also 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.
  • In the N-BOC-ylation of amides.
  • In the N-BOC-ylation of sensitive compounds under non-aqueous conditions.
Reagent for the introduction of the Boc protecting group.

Disclaimer

Hydrolyzes to t-butanol and CO2; causes internal pressure in bottle if exposed to moisture.

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.

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)

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL9400
BCCH2569
BCCK7558
BCCH9765
BCCG7958

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Boc-L-Dmt-OH as a fully N,S-blocked cysteine derivative for peptide synthesis by prior thiol capture. Facile conversion of N-terminal Boc-L-Dmt-peptides to H-Cys(Scm)-peptides
Kemp DS and Carey RI
The Journal of Organic Chemistry, 54(15), 3640-3646 (1989)
Di-tert-butyl Dicarbonate and 4-(Dimethylamino) pyridine Revisited. Their Reactions with Amines and Alcohols1
Basel Y and Hassner A
The Journal of Organic Chemistry, 65(20), 6368-6380 (2000)
Identification and characterization of N-tert-butoxycarbonyl-MDMA: a new MDMA precursor.
Collins M, et al.
Drug Testing and Analysis, 9(3), 399-404 (2017)
Profiling ephedrine prepared from N-methylalanine via the Akabori-Momotani Reaction.
Doddridge A, et al.
Drug Testing and Analysis, 10(3), 548-556 (2018)
Use of Di-tert-butyl-dicarbonate Both as a Protecting and Activating Group in the Synthesis of Dipeptides
Jhaumeer LS, et al.
Synthetic Communications, 37(23), 4191-4197 (2007)
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