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33482

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

Name: 1,8-Diazabicyclo[5.4.0]undec-7-ene
Brand: SIAL

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

Assay:

≥99.0% (GC)

Form:

liquid

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vapor pressure

7.1 hPa ( 37.7 °C)

Quality Level

200

grade

puriss.

assay

≥99.0% (GC)

form

liquid

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

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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Caustic Alkalis & Bases

Chemistry & Biochemicals

Lab Chemicals

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General description

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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.

pictograms

GHS06,GHS05

signalword

Danger

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

hcodes

H301,H314

pcodes

P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363 - P405

Hazard Classifications

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

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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)