1,8-Diazabicyclo(5.4.0)undec-7-ene

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The correct title of this article is 1,8-Diazabicyclo[5.4.0]undec-7-ene. The substitution of any brackets is due to technical restrictions.
1,8-Diazabicyclo[5.4.0]undec-7-ene
DBU molecule
Names
Preferred IUPAC name
2,3,4,6,7,8,9,10-Octahydropyrimido[1,2-a]azepine
Other names
DBU, Diazabicycloundecene
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.027.013 Edit this at Wikidata
EC Number
  • 229-713-7
UNII
  • InChI=1S/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2 checkY
    Key: GQHTUMJGOHRCHB-UHFFFAOYSA-N checkY
  • 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 152.241 g·mol−1
Appearance Colorless liquid
Density 1.018 g/mL liquid
Melting point −70 °C (−94 °F; 203 K)
Boiling point 261 °C (502 °F; 534 K) (1 atm),
80 to 83 °C (0.6 mmHg)
ethers, alcohols
Acidity (pKa) 13.5±1.5[1] (pKa of conjugate acid in water); 24.34[2] (pKa of conjugate acid in acetonitrile)
Hazards
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Danger
H301, H302, H312, H314, H412
P260, P264, P270, P273, P280, P301+P310, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P405, P501
Flash point 119.9 °C (247.8 °F; 393.0 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

1,8-Diazabicyclo[5.4.0]undec-7-ene, or more commonly DBU, is a

catalyst, a complexing ligand, and a non-nucleophilic base.[3]

Occurrence

Although all commercially available DBU is produced synthetically, it may also be isolated from the sea sponge

1,3-diaminopropane
.

Proposed pathway for the biosynthesis of DBU in sponges.[4]

Uses

As a reagent in organic chemistry, DBU is used as a ligand and base. As a base, protonation occurs at the imine nitrogen.[5] Lewis acids also attach to the same nitrogen.[6]

These properties recommend DBU for use as a catalyst, for example as a

curing agent for epoxy resins and polyurethane
.

It is used in the separation of fullerenes in conjunction with trimethylbenzene. It reacts with C70 and higher fullerenes, but not with C60.

It is useful for dehydrohalogenations.[7]

See also

References

  1. doi:10.5562/cca2472
    .
  2. PMID 15675863
    .
  3. doi:10.1055/s-2004-815436
    .
  4. ^
    PMID 20839615
    .
  5. ISSN 1864-5631
    .
  6. ISSN 2520-1158
    .
  7. ISBN 0-471-93623-5
    .
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