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

Boiling point:

95-98 °C7.5 mm Hg(lit.)

Density 

1.005 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.519(lit.)

Flash point:

202 °F

storage temp. 

Store below +30°C.

solubility 

soluble in Chloroform, Methanol

form 

Liquid

pka

13.42±0.20(Predicted)

color 

Clear colorless to yellow

Water Solubility 

soluble

Sensitive 

Air Sensitive

BRN 

2417

InChIKey

SGUVLZREKBPKCE-UHFFFAOYSA-N

CAS DataBase Reference

3001-72-7(CAS DataBase Reference)

NIST Chemistry Reference

1,5-diazabicyclo[4.3.0]non-5-ene(3001-72-7)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3267 8/PG 2

WGK Germany 

3

F 

1-3-8-10

Hazard Note 

Corrosive/Air Sensitive

HazardClass 

8

PackingGroup 

II

HS Code 

29335995

MSDS

• Language:English Provider:1,5-Diazabicyclo[4.3.0]non-5-ene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

1,5-Diazabicyclo[4.3.0]non-5-ene Usage And Synthesis

Description

1,5-Diazabicyclo [4.3.0]non-5-ene is a amidine base used in organic synthesis. It is employed for dehydrohalogenation reactions as well as base-catalyzed rearrangements. It can also be used as the nucleophilic catalyst for the Friedel-Crafts acylation of pyrroles and indoles2. Further, it is used as a resin curing agent and polyurethane catalyst.

Reference

Taylor, James E., et al. "Friedel−Crafts Acylation of Pyrroles and Indoles using 1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) as a Nucleophilic Catalyst." Cheminform 42.13(2015):5740.

Chemical Properties

clear colorless to yellowish liquid

Uses

1,5-Diazabicyclo[4.3.0]non-5-ene is employed for dehydrohalogenation reactions and base-catalyzed rearrangements in organic synthesis. It is an amidine base used in organic synthesis. Further, it is used as a resin curing agent and polyurethane catalyst.

Uses

• 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.

Definition

ChEBI: 1,5-diazabicyclo[4.3.0]-non-5-ene is a pyrrolopyrimidine.

Purification Methods

Distil DBN from BaO. It forms a hydroiodide on addition of 47% HI; dry it and dissolve it in MeCN, evaporate and repeat; recrystallise from EtOH, dry at 25o/1mm for 5hours, then at 80o/0.03mm for 12hours and store and dispense it in a dry box, m 154-156o [Jaeger et al. J Am Chem Soc 101 717 1979]. The methiodide is recrystallised from CHCl3/Et2O, m 248-250o, and hydrogen fumarate has m 159-160o and is crystallised from iso-PrOH [Rokach et al. J Med Chem 22 237 1979, Oediger et al. Chem Ber 99 2012 1966, Reppe et al. Justus Liebigs Ann Chem 596 210 1955]. [Beilstein 23/5 V 239.]

1,5-Diazabicyclo[4.3.0]non-5-ene(3001-72-7)Related Product Information

• DBU
• 1-NONENE
• Dicyclopentadiene
• 1,2-Dimethyl-1,4,5,6-tetrahydropyrimidine
• N-METHYL-1,3-PROPANEDIAMINE
• Methyl hexanoate
• 1-(3-Aminopropyl)pyrrolidine
• Propionamidine hydrochloride
• 1-Methylpyrrolidine
• 3-Dimethylaminopropylamine
• N-Ethyl-1,3-propanediamine
• N-PROPYL-1,3-PROPANEDIAMINE
• N,N'-Diethyl-1,3-propanediamine
• BUTYRAMIDINE
• 1,3-Diaminopropane
• N-PROPYLETHYLIDENEAMINE
• 1,4,5,6-TETRAHYDROPYRIMIDINE
• 1,5-Diazabicyclo[4.3.0]non-5-ene