34660

Di-tert-butyl dicarbonate

≥98.0% (GC), for peptide synthesis

• Synonyma: Boc₂O, Boc anhydride, Di-tert-butyl pyrocarbonate
• Lineární vzorec: [(CH₃)₃COCO]₂O
• Číslo CAS: 24424-99-5
• Molekulová hmotnost: 218.25
• NACRES: NA.22
• PubChem Substance ID: 329755051
• UNSPSC Code: 12352108
• EC Number: 246-240-1
• MDL number: MFCD00008805
• Beilstein/REAXYS Number: 1911173

Vlastnosti

• Název produktu: Di-tert-butyl dicarbonate, ≥98.0% (GC)
• Quality Segment: 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
• functional group: carbonate
• 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

Popis

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

Reagent for the introduction of the Boc protecting group.

Di-tert-butyl dicarbonate (Boc₂O) has been used in the synthesis of:

• An azobenzene amino acid(aa).[1]
• 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.

Disclaimer

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

Bezpečnostní informace

• pictograms: GHS02,GHS06,GHS05
• signalword: Danger
• hcodes: H226,H315,H317,H318,H330,H335
• pcodes: 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
• Skladovací třída: 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