34660

Di-tert-butyl dicarbonate

≥98.0% (GC), for peptide synthesis

• Synonym(s): Boc₂O, Boc anhydride, Di-tert-butyl pyrocarbonate
• 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: 12352108
• PubChem Substance ID: 329755051
• NACRES: NA.22

Properties

• Quality Level: 200
• 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
• 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.

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)

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.

Warning

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

Safety Information

• Pictograms: GHS02,GHS06,GHS05
• Signal Word: Danger
• Hazard Statements: H226,H315,H317,H318,H330,H335
• Precautionary Statements: P210 - P233 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• 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
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves