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Merck
CN

33482

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

greener alternative

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
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
329754558
EC Number:
229-713-7
Beilstein/REAXYS Number:
508906
MDL number:
MFCD00006930

Key Documents

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Product Name

1,8-Diazabicyclo[5.4.0]undec-7-ene, puriss., ≥99.0% (GC)

InChI key

GQHTUMJGOHRCHB-UHFFFAOYSA-N

InChI

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

SMILES string

C1CCN2CCCN=C2CC1

vapor pressure

7.1 hPa ( 37.7 °C)

grade

puriss.

assay

≥99.0% (GC)

form

liquid

Quality Level

200

greener alternative product characteristics

Catalysis
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refractive index

n20/D 1.523

pH

(12,8 at 10 g/l at 20 °C)

bp

115 °C/11 mmHg (lit.)

mp

-70  °C

density

1.019 g/mL at 20 °C (lit.)

greener alternative category

Aligned

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

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.

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

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

Storage Class

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

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN4364
BCCH0141
BCCK2213
BCCF4630
BCCC1265

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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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