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

1,5-Diazabicyclo[4.3.0]non-5-ene Basic information
Description Reference
Product Name:1,5-Diazabicyclo[4.3.0]non-5-ene
Synonyms:1,5-Diazabicyclo[4.3.0]non-5-ene,DBN;1,5-DIAZABICYCLO[4.3.0]NON-5-ENE FOR SYN;1,5-Diazabicyclo[4.3.0]non-5-ene purum, >=98.0% (GC);DBN 1,5-Diazabicyclo[4.3.0]non-5-ene;2H,3H,4H,6H,7H,8H-Pyrrolo[1,2-a]pyrimidine;1,5-Diazabicyclo[4.3.0]non-5-ene≥ 99%(GC);Diazabicyclononene (DBN);1,5-DiazabicycL
CAS:3001-72-7
MF:C7H12N2
MW:124.18
EINECS:221-087-3
Product Categories:
Mol File:3001-72-7.mol
1,5-Diazabicyclo[4.3.0]non-5-ene Structure
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.)
Fp 202 °F
storage temp. Store below +30°C.
solubility soluble in Chloroform, Methanol
form Liquid
pka13.42±0.20(Predicted)
color Clear colorless to yellow
Water Solubility soluble
Sensitive Air Sensitive
BRN 2417
InChIKeySGUVLZREKBPKCE-UHFFFAOYSA-N
CAS DataBase Reference3001-72-7(CAS DataBase Reference)
NIST Chemistry Reference1,5-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
1-3-8-10
Hazard Note Corrosive/Air Sensitive
HazardClass 8
PackingGroup II
HS Code 29335995
MSDS Information
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1,5-Diazabicyclo[4.3.0]non-5-ene Usage And Synthesis
Description1,5-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.
ReferenceTaylor, 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 Propertiesclear colorless to yellowish liquid
Uses1,5-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.

DefinitionChEBI: 1,5-diazabicyclo[4.3.0]-non-5-ene is a pyrrolopyrimidine.
Purification MethodsDistil 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 Preparation Products And Raw materials
Raw materialsSodium azide-->Tosyl chloride-->Oxalyl chloride-->1,2-Dichloroethane-->Anisole-->2-Pyrrolidinone-->3-Chloro-1-propanol
Preparation Products5-Dibenzosuberenone
1-Methylpyrrolidine Propionamidine hydrochloride 1-(3-Aminopropyl)pyrrolidine 1,4,5,6-TETRAHYDROPYRIMIDINE Dicyclopentadiene N-Ethyl-1,3-propanediamine 3-Dimethylaminopropylamine Rofelodine N-PROPYL-1,3-PROPANEDIAMINE N,N'-Diethyl-1,3-propanediamine N-METHYL-1,3-PROPANEDIAMINE 1-NONENE BUTYRAMIDINE 1,5-Diazabicyclo[4.3.0]non-5-ene DBU 1,2-Dimethyl-1,4,5,6-tetrahydropyrimidine 1,3-Diaminopropane N-PROPYLETHYLIDENEAMINE

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