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33471

Sigma-Aldrich

1,5-Diazabicyclo[4.3.0]non-5-ene

purum, ≥98.0% (GC)

Synonym(s):

DBN

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About This Item

Empirical Formula (Hill Notation):
C7H12N2
CAS Number:
Molecular Weight:
124.18
Beilstein:
2417
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

grade

purum

Quality Level

Assay

≥98.0% (GC)

form

liquid

impurities

≤1% water

refractive index

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

bp

95-98 °C/7.5 mmHg (lit.)

density

1.005 g/mL at 25 °C (lit.)

SMILES string

C1CN=C2CCCN2C1

InChI

1S/C7H12N2/c1-3-7-8-4-2-6-9(7)5-1/h1-6H2

InChI key

SGUVLZREKBPKCE-UHFFFAOYSA-N

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Application

  • 1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) is an amidine base commonly used in the base-mediated eliminations, condensations, esterifications, isomerizations, carboxylations and carbonylations.
  • It is used in the preparation of supertetrahedral chalcogenide clusters and single crystals of polymer-chalcogenide composites.
  • It also acts as a catalyst for the regioselective Friedel-Crafts C-acylation of pyrroles.

Other Notes

Amidine base used for dehydrohalogenation reactions to olefins

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

201.2 °F - closed cup

Flash Point(C)

94 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Nucleophilicities and carbon basicities of DBU and DBN.
Baidya, M and Mayr, Herbert
Chemical Communications (Cambridge, England), 1792-1794 (2008)
H. Oediger et al.
Synthesis, 591-591 (1972)
1, 5-Diazabicyclo [4.3. 0] non-5-ene.
Savoca, Ann C and Urgaonkar, Sameer
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Superbase route to supertetrahedral chalcogenide clusters.
Wu, Tao et al.
Journal of the American Chemical Society, 134(8), 3619-3622 (2012)
Ryuichi Arakawa et al.
Journal of mass spectrometry : JMS, 40(1), 66-69 (2004-12-08)
When elemental selenium was added to a strongly basic amine, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), the selenium started to dissolve and the solution turned dark brown. We investigated the chemical reaction of this selenium dissolution process by electrospray ionization mass

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