Diazabicycloundecene
Structural formula | |||||||||||||||||||
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General | |||||||||||||||||||
Surname | 1,8-diazabicyclo [5.4.0] undec-7-ene | ||||||||||||||||||
other names |
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Molecular formula | C 9 H 16 N 2 | ||||||||||||||||||
Brief description |
colorless liquid |
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properties | |||||||||||||||||||
Molar mass | 152.24 g mol −1 | ||||||||||||||||||
Physical state |
liquid |
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density |
1.02 g cm −3 (at 20 ° C ) |
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Melting point |
−70 ° C |
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boiling point |
261 ° C |
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Vapor pressure | |||||||||||||||||||
pK s value |
12 (protonated) |
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solubility |
soluble in water |
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safety instructions | |||||||||||||||||||
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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
- ↑ a b c d e f Data sheet 1,8-Diazabicyclo [5.4.0] undec-7-en (PDF) from Merck , accessed on March 24, 2011.
- ↑ pKA values of selected representatives of different classes of compounds from ETH Zurich
- ↑ 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) .
- ↑ 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 .