1,8-Diazabicycloundec-7-ene

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
Names


IUPAC name 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine
Other names DBU,Diazabicycloundecene
Identifiers
CAS Registry Number	6674-22-2^Y
ChemSpider	73246^Y
InChI InChI=1S/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2^Y Key: GQHTUMJGOHRCHB-UHFFFAOYSA-N^Y InChI=1/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2 Key: GQHTUMJGOHRCHB-UHFFFAOYAM
Jmol-3D images	Image
SMILES N\2=C1\N(CCCCC1)CCC/2
Properties
Chemical formula	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 (pK_a)	13.5±1.5^[1] (pK_a of conjugate acid in water); 24.34^[2] (pK_a of conjugate acid in acetonitrile)
Hazards
R-phrases	R22 R34
S-phrases	S24 S25
Flash point	119.9 °C (247.8 °F; 393.0 K)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Y verify (what is: Y/N?)
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.

This compound is also an alkaloid isolated from the sponge Niphates digitalis.^[3]

Regalado hypothetic biosynthesis of DBU

It is used as a curing agent for epoxy; it is used as a protecting agent for the synthesis of cephalosporin. It is used in fullerene purification with trimethylbenzene (it reacts to C70 and higher fullerenes but not to C60 fullerenes); and it is also used as a catalyst for polyurethane. It has a strong catalyst effect for the reactions of alicyclic and aliphatic isocyanates.

References

↑ 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. doi:10.1021/jo048252w. PMID 15675863.
↑ Regalado, E.L. et al., Nat. Prod. Commun., 2010, 5, 1187- 1190

1,8-Diazabicycloundec-7-ene

See also

References