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33482

Sigma-Aldrich

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

puriss., ≥99.0% (GC)

Synonym(s):

2,3,4,6,7,8,9,10-Octahydropyrimidol[1,2-a]azepine, DBU

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About This Item

Empirical Formula (Hill Notation):
C9H16N2
Molecular Weight:
152.24
Beilstein:
508906
EC Number:
229-713-7
MDL number:
MFCD00006930
UNSPSC Code:
12352005
PubChem Substance ID:
329754558
NACRES:
NA.22

grade

puriss.

Quality Level

200

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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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

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H290,H301,H314,H412

Hazard Classifications

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

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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H. Oediger et al.
Synthesis, 591-591 (1972)
N. Ono et al.
Bulletin of the Chemical Society of Japan, 52, 1716-1716 (1979)
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)
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)
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