34660

Sigma-Aldrich

Di-tert-butyl dicarbonate

≥98.0% (GC)

Sinónimos:
Di-tert-butyl pyrocarbonate, Boc anhydride, Boc2O
Fórmula lineal:
[(CH3)3COCO]2O
Número de CAS:
Peso molecular:
218.25
Beilstein/REAXYS Number:
1911173
Número de EC:
Número MDL:
ID de la sustancia en PubChem:
NACRES:
NA.22

Nivel de calidad

200

ensayo

≥98.0% (GC)

aplicaciones

peptide synthesis: suitable

índice de refracción

n20/D 1.409 (lit.)

bp

56-57 °C/0.5 mmHg (lit.)

mp

23 °C (lit.)

densidad

0.95 g/mL at 25 °C (lit.)

temp. de almacenamiento

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

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Descripción general

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.

Aplicación

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.

Envase

25, 100, 500 g in poly bottle

Advertencia

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

Palabra de señalización

Danger

hazcat

Acute Tox. 1 Inhalation - Eye Dam. 1 - Flam. Liq. 3 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Órganos de actuación

Respiratory system

storage_class_code

3 - Flammable liquids

WGK Alemania

WGK 3

Punto de inflamabilidad F

98.6 °F - closed cup

Punto de inflamabilidad C

37 °C - closed cup

Equipo de protección personal

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificado de Análisis

Certificado de origen

Exhaustive tert-Butoxycarbonylation of Peptide Nitrogens
L. Grehn and Ragnarsson U
Angewandte Chemie (International Edition in English), 24(6), 510-511 (1985)
A mild two-step method for the hydrolysis of lactams and secondary amides
D.L. Flynn et al.
The Journal of Organic Chemistry, 48(14), 2424-2426 (1983)
A new efficient synthesis of isothiocyanates from amines using di-tert-butyl dicarbonate
Munch H, et al.
Tetrahedron Letters, 49(19), 3117-3119 (2008)
Synthesis of chiral oxazolidin-2-ones and imidazolidin-2-ones via DMAP-catalyzed isocyanation of amines with di-tert-butyl dicarbonate
Knolker H-J and Braxmeier T
Tetrahedron Letters, 39(51), 9407-9410 (1998)
Pd-catalyzed decarbonylative Heck olefination of aromatic carboxylic acids activated in situ with di-tert-butyl dicarbonate
Goossen LJ, et al.
Synlett, 2002(10), 1721-1723 (2002)

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