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136581

Sigma-Aldrich

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

98%

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:
2417
EC Number:
221-087-3
MDL number:
MFCD00005554
UNSPSC Code:
12352005
PubChem Substance ID:
24848287
NACRES:
NA.22

Assay

98%

form

liquid

refractive index

n20/D 1.519 (lit.)

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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General description

DBN is a strong base widely used as a catalyst in organic synthesis to facilitate Michael additions and aldol condensations.

Application

1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) can be used as:      
  •   A reagent for the synthesis of β-carbolines from tetrahydro-β-carbolines via dehydrogenative/decarboxylative aromatization.       
  • A nucleophilic organocatalyst in the regioselective C-acylation of pyrroles and indoles by Friedel−Crafts acylation reaction.
  •   A superbase in the formulation of a ternary liquid-liquid phase changing system, along with hexadecane and hexanol, to capture hydrogen sulfide gas.      
  • A base for the preparation of 1H-quinazoline-2,4-diones from 2-aminobenzonitriles using supercritical carbon dioxide as a reactant and a solvent.
  •   A catalyst for the synthesis of benzothiazolones by the reaction between 2-aminothiophenols and CO2 by cyclocarbonylation reaction via C-S bond formation.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The simple solvent-free synthesis of 1H-quinazoline-2, 4-diones using supercritical carbon dioxide and catalytic amount of base
Mizuno T, et al.
Tetrahedron Letters, 45(38), 7073-7075 (2004)
Organic base-promoted efficient dehydrogenative/decarboxylative aromatization of tetrahydro-βcarbolines into β-carbolines under air.
Zhao Z, et al.
Tetrahedron Letters, 60(11), 800-804 (2019)
Phase-Change Reversible Absorption of Hydrogen Sulfide by the Superbase 1, 5-Diazabicyclo [4.3. 0] non-5-ene in Organic Solvents.
Xu Z, et al.
Industrial & Engineering Chemistry Research, 58(4), 1701-1710 (2019)
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
Arinze Akutekwe et al.
IET systems biology, 9(6), 294-302 (2015-11-19)
Accurate and reliable modelling of protein-protein interaction networks for complex diseases such as colorectal cancer can help better understand mechanism of diseases and potentially discover new drugs. Different machine learning methods such as empirical mode decomposition combined with least square
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