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33482

Sigma-Aldrich

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

puriss., ≥99.0% (GC)

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Synonym(s):
2,3,4,6,7,8,9,10-Octahydropyrimidol[1,2-a]azepine, DBU
Empirical Formula (Hill Notation):
C9H16N2
Molecular Weight:
152.24
Beilstein:
508906
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

grade

puriss.

Quality Level

Assay

≥99.0% (GC)

form

liquid

refractive index

n20/D 1.523

bp

115 °C/11 mmHg (lit.)

density

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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This Item
33471136581139009
assay

≥99.0% (GC)

assay

≥98.0% (GC)

assay

98%

assay

98%

form

liquid

form

liquid

form

liquid

form

liquid

refractive index

n20/D 1.523

refractive index

n20/D 1.519 (lit.), n20/D 1.521

refractive index

n20/D 1.519 (lit.)

refractive index

n20/D 1.522-1.524 (lit.)

bp

115 °C/11 mmHg (lit.)

bp

95-98 °C/7.5 mmHg (lit.)

bp

95-98 °C/7.5 mmHg (lit.)

bp

80-83 °C/0.6 mmHg (lit.)

density

1.019 g/mL at 20 °C (lit.)

density

1.005 g/mL at 25 °C (lit.)

density

1.005 g/mL at 25 °C (lit.)

density

1.018 g/mL at 25 °C (lit.)

Application

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.

Other Notes

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

Pictograms

CorrosionSkull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 2

Flash Point(F)

240.8 °F

Flash Point(C)

116 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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N. Ono et al.
Bulletin of the Chemical Society of Japan, 51, 2401-2401 (1978)
C.G. Rao
Organic preparations and procedures international, 12, 225-225 (1980)
1, 8-Diazabicyclo [5.4. 0] undec-7-ene (DBU): A highly efficient catalyst in glycerol carbonate synthesis.
Munshi MK, et al.
J. Mol. Catal. A: Chem., 391, 144-149 (2014)
H. Oediger et al.
Synthesis, 591-591 (1972)
N. Ono et al.
Bulletin of the Chemical Society of Japan, 52, 1716-1716 (1979)

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