3D model (JSmol)
|Molar mass||152.24 g/mol|
|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 (pKa of conjugate acid in water); 24.34 (pKa of conjugate acid in acetonitrile)|
|R-phrases (outdated)||R22 R34|
|S-phrases (outdated)||S24 S25|
|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).
|what is ?)(|
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.
Although all DBU is produced synthetically, it can also be isolated from the sea sponge Niphates digitalis. The biosynthesis of DBU has been proposed to begin with 1,8-octanedial (suberic aldehyde) and 1,3-diaminopropane.
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. It also exhibited its dual character (base and nucleophile) in the synthesis of aryl- & styryl- terminal acetylenes.
- Kaupmees, K.; Trummal, A.; Leito, I. (2014). "Basicities of Strong Bases in Water: A Computational Study". Croat. Chem. Acta. 87: 385–395. doi:10.5562/cca2472.
- Kaljurand, I.; Kütt, A.; Sooväli, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I. A. (2005). "Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pKa Units: Unification of Different Basicity Scales". J. Org. Chem. 70: 1019–1028. PMID 15675863. doi:10.1021/jo048252w.
- Regalado, E.L. et al., Nat. Prod. Commun., 2010, 5, 1187- 1190
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