Diazabicycloundecene

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of DBU
General
Surname 1,8-diazabicyclo [5.4.0] undec-7-ene
other names
  • 1,8-diazabicyclo [5.4.0] undec-7-en ( IUPAC )
  • DBU
Molecular formula C 9 H 16 N 2
Brief description

colorless liquid

External identifiers / databases
CAS number 6674-22-2
EC number 229-713-7
ECHA InfoCard 100.027.013
PubChem 81184
ChemSpider 73246
Wikidata Q306166
properties
Molar mass 152.24 g mol −1
Physical state

liquid

density

1.02 g cm −3 (at 20 ° C )

Melting point

−70 ° C

boiling point

261 ° C

Vapor pressure

2 Pa at 25 ° C

pK s value

12 (protonated)

solubility

soluble in water

safety instructions
GHS labeling of hazardous substances
06 - Toxic or very toxic 05 - Corrosive

danger

H and P phrases H: 301-314-412-290
P: 273-280-301 + 310-305 + 351 + 338-310
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,8-Diazabicyclo [5.4.0] undec-7-en , abbreviated DBU , is a fused amidine base with the empirical formula C 9 H 16 N 2 .

Properties and use

DBU is a colorless liquid that can be freely mixed with water and is also soluble in many organic solvents . The non- nucleophilic strong base ( pKa value of the protonated form = 12) is mostly used to deprotonate CH-acidic substances, similar to the structurally related compound 1,5-diazabicyclo [4.3.0] non-5-en (DBN) . DBU is also used as a labile ligand in complex chemistry or as a base in the Baylis-Hillman reaction , in which DBU can replace DABCO .

Individual evidence

  1. ↑ a b c d e f Data sheet 1,8-Diazabicyclo [5.4.0] undec-7-en Template: Linktext-Check / Escaped (PDF) from Merck , accessed on March 24, 2011.
  2. ↑ pKA values ​​of selected representatives of different classes of compounds from ETH Zurich
  3. ↑ a b Entry on 1,8-diazabicyclo (5.4.0) undec-7-en in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
  4. ↑ Kristin E. Price, Steven J. Broadwater, Brian J. Walker, D. Tyler McQuade: A New Interpretation of the Baylis − Hillman Mechanism . In: J. Org. Chem. 2005, 70 , 3980-3987. doi : 10.1021 / jo050202j .