Bicarbonato di-terc-butílico

≥98.0% (GC), for peptide synthesis

Sinônimo(s):

Anidrido Boc, Pirocarbonato di-terc-butílico

Fórmula linear:

[(CH₃)₃COCO]₂O

CAS Number:

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

Product Name

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 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.[1][2]

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).[3]
• N-tert-butoxycarbonyl-3,4-methylenedioxymethamphetamine (t-BOC-MDMA) from MDMA.[4][5]

It can also be used as a reagent:

• To introduce acid-labile Boc-protecting group in amino acids, peptides, and proteins.[1][6]        
• To prepare styrene derivatives by Heck olefination of aromatic carboxylic acids in the presence of a Pd catalyst.[7]        
• To synthesize oxazolidin-2-ones and imidazolidin-2-ones by isocyanation of 1,2-aminoalcohols and 1,2-diamines using DMAP as a catalyst.[8]       
• In the preparation of N-tert-butoxycarbonyl-3,4-methylenedioxymethamphetamine (t-Boc-MDMA) from MDMA.[4]
• For the conversion of amines to corresponding isocyanates, carbamates, and urea derivatives.[9]
• In the N-BOC-ylation of amides.[10][11]
• In the N-BOC-ylation of sensitive compounds under non-aqueous conditions.[12]

Exoneração de responsabilidade

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