Merck
All Photos(1)

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
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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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.[1]
  • As a nucleophilic catalyst for the esterification of carboxylic acid with dimethyl carbonate.[2]
  • As a bidentate ligand in copper (I) bromide mediated atom transfer radical polymerization of methyl methacrylate.[3]
  • As an efficient catalyst for the transesterification of dimethyl carbonate with glycerol.[4]

Other Notes

Amidine base used for dehydrohalogenation reactions to olefins[5]; Further important applications are e.g.: esterification of carboxylic acids with alkyl halides[6][7]; Alkylation and acylation of active methylene compounds[8]

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


Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

Certificate of Analysis

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Certificate of Origin

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