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33482

Sigma-Aldrich

1,8-Diazabicyclo[5.4.0]undec-7-ene

puriss., ≥99.0% (GC)

Sinônimo(s):
DBU, 2,3,4,6,7,8,9,10-Octahydropyrimidol[1,2-a]azepine
Empirical Formula (Hill Notation):
C9H16N2
Peso molecular:
152.24
Beilstein:
508906
Número EC:
Número MDL:
ID de substância PubChem:
NACRES:
NA.22

grau

puriss.

Nível de qualidade

200

teor

≥99.0% (GC)

índice de refração

n20/D 1.523

pb

115 °C/11 mmHg (lit.)

densidade

1.019 g/mL at 20 °C (lit.)

SMILES string

C1CCN2CCCN=C2CC1

InChI

1S/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2

InChI key

GQHTUMJGOHRCHB-UHFFFAOYSA-N

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Aplicação

1,8-Diazabicyclo[5.4.0]undec-7-ene can be used:
  • To mediate the aza-Michael addition of nitrogen nucleophiles to α,β-unsaturated carbonyl compounds.
  • As a nucleophilic catalyst for the esterification of carboxylic acid with dimethyl carbonate.
  • As a bidentate ligand in copper (I) bromide mediated atom transfer radical polymerization of methyl methacrylate.
  • As an efficient catalyst for the transesterification of dimethyl carbonate with glycerol.

Outras notas

Amidine base used for dehydrohalogenation reactions to olefins; Further important applications are e.g.: esterification of carboxylic acids with alkyl halides; Alkylation and acylation of active methylene compounds

Pictogramas

CorrosionSkull and crossbones

Palavra indicadora

Danger

Classificações de perigo

Acute Tox. 3 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Met. Corr. 1 - Skin Corr. 1B

Código de classe de armazenamento

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Ponto de fulgor (ºF)

240.8 °F

Ponto de fulgor (ºC)

116 °C

Equipamento de proteção individual

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

Certificado de análise

Certificado de origem

N. Ono et al.
Bulletin of the Chemical Society of Japan, 52, 1716-1716 (1979)
H. Oediger et al.
Synthesis, 591-591 (1972)
1, 8-Diazabicyclo [5.4. 0] undec-7-ene (DBU) as ligand for atom transfer radical polymerization (ATRP)
Fournier D, et al.
European Polymer Journal, 41(7), 1576-1581 (2005)
C.G. Rao
Organic preparations and procedures international, 12, 225-225 (1980)
N. Ono et al.
Bulletin of the Chemical Society of Japan, 51, 2401-2401 (1978)

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