1,8-Diazabicycloundec-7-ene

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The correct title of this article is 1,8-Diazabicyclo[5.4.0]undec-7-ene. The substitution or omission of any < > [ ] { } is because of technical restrictions.
1,8-Diazabicyclo[5.4.0]undec-7-ene
DBU.svg
DBU molecule
Names
IUPAC name
2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine
Other names
DBU,Diazabicycloundecene
Identifiers
6674-22-2 YesY
ChemSpider 73246 YesY
Jmol 3D model Interactive image
  • InChI=1S/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2 YesY
    Key: GQHTUMJGOHRCHB-UHFFFAOYSA-N YesY
  • InChI=1/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2
    Key: GQHTUMJGOHRCHB-UHFFFAOYAM
  • N\2=C1\N(CCCCC1)CCC/2
Properties
C9H16N2
Molar mass 152.24 g/mol
Appearance Colorless liquid
Density 1.018 g/mL liquid
Melting point −70 °C (−94 °F; 203 K)
Boiling point 80 to 83 °C (176 to 181 °F; 353 to 356 K) (0.6 mmHg); 261 °C (1 atm)
Acidity (pKa) 13.5±1.5[1] (pKa of conjugate acid in water); 24.34[2] (pKa of conjugate acid in acetonitrile)
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

1,8-Diazabicyclo[5.4.0]undec-7-ene, or more commonly DBU, is a chemical compound and belongs to the class of amidine compounds. It is used in organic synthesis as a catalyst, a complexing ligand, and a non-nucleophilic base.

Occurrence

Although DBU is typically produced synthetically, it is also an alkaloid isolated from the sponge Niphates digitalis.[3] The biosynthesis of DBU has been proposed to begin with suberic aldehyde and diaminopropane.[3]

Hypothetical biosynthesis of DBU

Uses

As a reagent in organic chemistry, DBU is used as a catalyst, a complexing ligand, and a non-nucleophilic base. It is also used as a curing agent for epoxy. It is used in fullerene purification with trimethylbenzene (it reacts with C70 and higher fullerenes, but not to C60 fullerenes); and it is also used as a catalyst in polyurethane production. It has a strong catalyst effect for the reactions of alicyclic and aliphatic isocyanates.

See also

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ 3.0 3.1 Regalado, E.L. et al., Nat. Prod. Commun., 2010, 5, 1187- 1190

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