DBU

(1,8-Diazabicyclo[5.4.0]undec-7-ene)

Other Names:

2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine

General Information:

Structure:

CAS Number: 6674-22-2

Molecular Weight: 152.24 g/mol

Appearance: Colorless to light yellow liquid

Density: 1.018 g/mL at 25 C

DBU is considered to be a non-nucleophilic base. DBU can serve as a base, catalyst, or complexing ligand in a wide variety of reactions.

Common Uses:

Reagent for conversion of alcohols to azides (DPPA + DBU)

Procedure excerpt:

To a suspension of the SM (0.665 g, 1.66 mmol) in THF (10 mL) at RT under Ar was added DPPA (0.400 mL, 1.83 mmol) and DBU (0.297 mL, 1.99 mmol). The resulting mixture . . .

[full procedure]

Catalyst in some Michael addition reactions

Procedure excerpt:

To a solution of the SM (0.5 g, 1.56 mmol) and 2-propyn-1-ol (5.0 mL, 85.86 mmol) was added DBU (0.035 mL, 0.23 mmol). The reaction mixture was stirred at RT for 16 h, then . . .

[full procedure]

References:

1) Patent Reference: WO2015144799, page 343, (18.8 MB)

2) Patent Reference: WO2014110000, page 30, (2.6 MB)

3) Wikipedia: 1,8-Diazabicyclo[5.4.0]undec-7-ene (link)

4) www.sigmaaldrich.com: 1,8-Diazabicyclo[5.4.0]undec-7-ene (link)

5) Reich, H. J.; Rigby, J. H.; Handbook of Reagents for Organic Synthesis, Acidic and Basic Reagents