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1,8-Diazabicyclo[5.4.0]undec-7-ene

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1,8-Diazabicyclo[5.4.0]undec-7-ene Basic information
1,8-Diazabicyclo[5.4.0]undec-7-ene Chemical Properties
  • Melting point:-70 °C
  • Boiling point:80-83 °C0.6 mm Hg(lit.)
  • Density 1.019 g/mL at 20 °C(lit.)
  • vapor pressure 5.3 mm Hg ( 37.7 °C)
  • refractive index n20/D 1.523
  • Flash point:>230 °F
  • storage temp. Store below +30°C.
  • solubility soluble
  • form Liquid
  • pka13.28±0.20(Predicted)
  • color Clear colorless to light yellow
  • PH12.8 (10g/l, H2O, 20℃)
  • OdorUnpleasant
  • PH Range12.8 at 10 g/l at 20 °C
  • explosive limit1.1-6.5%(V)
  • Water Solubility soluble
  • Sensitive Air Sensitive
  • BRN 508906
  • Stability:Stable. Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides.
  • InChIKeyGQHTUMJGOHRCHB-UHFFFAOYSA-N
  • CAS DataBase Reference6674-22-2(CAS DataBase Reference)
  • NIST Chemistry Reference1,8-diazabicyclo [5.4.0]undec-7-ene(6674-22-2)
  • EPA Substance Registry SystemPyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro- (6674-22-2)
Safety Information
  • Hazard Codes C,F
  • Risk Statements 22-34-52/53-35-40-37-19-11-67
  • Safety Statements 26-36/37/39-45-61-27-16
  • RIDADR UN 3267 8/PG 2
  • WGK Germany 2
  • 34
  • Autoignition Temperature260 °C
  • TSCA Yes
  • HazardClass 8
  • PackingGroup II
  • HS Code 29339930
  • ToxicityLD50 orally in Rabbit: 215 - 681 mg/kg
MSDS
1,8-Diazabicyclo[5.4.0]undec-7-ene Usage And Synthesis
  • Description1,8-Diazabicyclo[5.4.0]undec-7-ene is a bicyclic amidine base. It is non-nucleophilic, sterically hindered, tertiary amine base in organic chemistry. It is reported to be superior to amine catalyst in Baylis-Hillman reaction.It promotes the methylation reaction of phenols, indoles and benzimidazoles with dimethyl carbonate under mild conditions.
  • Chemical PropertiesColorless to yellow liquid
  • Uses1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) may be used:
    1. as catalyst for carboxylic acid esterification with dimethyl carbonate
    2. in the synthesis of duocarmycin and CC-1065 analogs
    3. as catalyst in aza-Michael addition and Knovenegal condensation reaction
    4. as base for dehalogenation of halogenated Diels-Alder adducts and the resulting activated 2,4-dienones were subjected to regio- and stereo-directed Michael additions, using Yamamoto′s reagent (CH3Cu · BF3)
    5. in a new synthesis of the ABCD ring system of Camptothecin
    6. 1,8-Diazabicyclo[5.4.0]undec-7-ene may be used as an catalyst for the dissolution and activation of cellulose by a reversible reaction of its hydroxyl groups with carbon dioxide. This dissolved cellulose system can be derivatized to form cellulose mixed esters.
    7. Used in a new synthesis of the ABCD ring system of Camptothecin.
  • Purification MethodsFractionally distil DBU under vacuum. Also purify it by chromatography on Kieselgel and eluting with CHCl3/EtOH/25% aqueous NH3 (15:5:2) and checking by IR and MS. [Oediger et al. Chem Ber 99 2012 1962, Angew Chem, Int Ed Engl 6 76 1967, Guggisberg et al. Helv Chim Acta 61 1057 1978, Beilstein 23/5 V 271.]
1,8-Diazabicyclo[5.4.0]undec-7-ene Preparation Products And Raw materials
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