3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||152.241 g·mol−1|
|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)|
|GHS Signal word||Danger|
|H301, H302, H312, H314, H318, H412|
|P260, P264, P270, P273, P280, P301+310, P301+312, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, 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).
|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 commercially available 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 1,6-hexanedial 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- and styryl-terminal acetylenes.
- Kaupmees, K.; Trummal, A.; Leito, I. (2014). "Basicities of Strong Bases in Water: A Computational Study". Croat. Chem. Acta. 87 (4): 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 (3): 1019–1028. doi:10.1021/jo048252w. PMID 15675863.
- Ghosh, Nandita (2004). "DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) - A Nucleophillic Base". Synlett (3): 574–575. doi:10.1055/s-2004-815436.
- Regalado, E.L. et al., Nat. Prod. Commun., 2010, 5, 1187- 1190