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 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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: | |
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).
|
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. [3]
Although all commercially available DBU is produced synthetically, it may also be isolated from the sea sponge Niphates digitalis. [4] The biosynthesis of DBU has been proposed to begin with adipaldehyde and 1,3-diaminopropane.
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]
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 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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: | |
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).
|
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. [3]
Although all commercially available DBU is produced synthetically, it may also be isolated from the sea sponge Niphates digitalis. [4] The biosynthesis of DBU has been proposed to begin with adipaldehyde and 1,3-diaminopropane.
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]