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

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1,5-Diazabicyclo[4.3.0]non-5-ene Basic information
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.
  • 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
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
  • 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
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