34660

Bicarbonato di-terc-butílico

≥98.0% (GC), for peptide synthesis

• Sinônimo(s): Anidrido Boc, Pirocarbonato di-terc-butílico
• Fórmula linear: [(CH₃)₃COCO]₂O
• Número CAS: 24424-99-5
• Peso molecular: 218.25
• Beilstein: 1911173
• Número CE: 246-240-1
• Número MDL: MFCD00008805
• Código UNSPSC: 12352108
• ID de substância PubChem: 329755051
• NACRES: NA.22

Propriedades

• Nome do produto: Bicarbonato di-terc-butílico, ≥98.0% (GC)
• Nível de qualidade: 200
• Ensaio: ≥98.0% (GC)
• Formulário: solid or liquid
• índice de refração: n20/D 1.409 (lit.)
• p.e.: 56-57 °C/0.5 mmHg (lit.)
• pf: 23 °C (lit.)
• densidade: 0.95 g/mL at 25 °C (lit.)
• aplicação(ões): peptide synthesis
• grupo funcional: carbonate
• temperatura de armazenamento: 2-8°C
• cadeia de caracteres SMILES: 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
• chave InChI: DYHSDKLCOJIUFX-UHFFFAOYSA-N

Descrição

Descrição geral

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)

Aplicação

Reagente para introdução do grupo protetor Boc.

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.

Advertência

Hidrolisa em t-butanol e CO₂; causa pressão interna no frasco, se exposto à umidade.

Informações de segurança

• Pictogramas: GHS02,GHS06,GHS05
• Palavra indicadora: Danger
• Frases de perigo: H226,H315,H317,H318,H330,H335
• Declarações de precaução: P210 - P233 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Classificações de perigo: Acute Tox. 1 Inhalation - Eye Dam. 1 - Flam. Liq. 3 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3
• Órgãos-alvo: Respiratory system
• Código de classe de armazenamento: 3 - Flammable liquids
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): 98.6 °F - closed cup
• Ponto de fulgor (°C): 37 °C - closed cup
• Equipamento de proteção individual: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter