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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:
3001-72-7
Molecular Weight:
124.18
Beilstein/REAXYS Number:
2417
EC Number:
221-087-3
MDL number:
MFCD00005554
UNSPSC Code:
12352005
PubChem Substance ID:
329754556
NACRES:
NA.22

grade

purum

Quality Level

200

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
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

201.2 °F - closed cup

flash_point_c

94 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCBT1403
BCBK7579V
BCBH3818V
BCBH3818V
BCBK7579V

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Nucleophilicities and carbon basicities of DBU and DBN.
Baidya, M and Mayr, Herbert
Chemical Communications (Cambridge, England), 1792-1794 (2008)
Threading chalcogenide layers with polymer chains.
Xiong, Wei-Wei et al.
Angewandte Chemie (International Edition in English), 127(2), 556-560 (2015)
Superbase route to supertetrahedral chalcogenide clusters.
Wu, Tao et al.
Journal of the American Chemical Society, 134(8), 3619-3622 (2012)
1, 5-Diazabicyclo [4.3. 0] non-5-ene.
Savoca, Ann C and Urgaonkar, Sameer
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Andrzej E Wróblewski et al.
The Journal of organic chemistry, 67(2), 420-425 (2002-01-19)
Although P(CH(3)NCH(2)CH(2))(3)N (1) was found to be less effective than 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in the removal of hydrogen bromide from vitamin A intermediates 13-cis-10-bromo-9,10-dihydroretinyl acetates (6) and 14-bromo-9,14-dihydroretinyl acetate (11) when the reaction was carried out in refluxing
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