1,5-diazabicyclo (4.3.0) non-5-en

Structural formula
General
Surname	1,5-diazabicyclo [4.3.0] non-5-ene
other names	DBN
Molecular formula	C 7 H 12 N 2
Brief description	light yellow liquid
External identifiers / databases
EC number	221-087-3
ECHA InfoCard	100.019.171
PubChem	76349
Wikidata	Q307070
properties
Molar mass	124.18 g mol −1
Physical state	liquid
density	1.005 g cm −3 (25 ° C)
boiling point	95-98 ° C / 7.5 mmHg
Refractive index	1.519 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 314
	P: 280-305 + 351 + 338-310
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

1,5-Diazabicyclo [4.3.0] non-5-en ( DBN ) is a chemical compound from the group of the bicyclic amidines .

properties

1,5-Diazabicyclo [4.3.0] non-5-en is a clear, light yellow liquid. It is a non- nucleophilic, very strong base which, with a pK value of 13.6, is almost as strong as sodium hydroxide. The voluminous bases can attack and bind easily accessible bound protons and therefore very successfully initiate elimination reactions . However, the bases are not able to attack shielded carbon atoms nucleophilically and therefore unwanted substitution reactions cannot occur as when using NaOH as the base .

The imino nitrogen, = NR, is protonated with the formation of a mesomeric-stabilized cation. The related connection DBU has similar properties .

use

1,5-Diazabicyclo [4.3.0] non-5-ene is used for dehydrohalogenation reactions to give olefins .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ data sheet 1,5-diazabicyclo [4.3.0] non-5-en, purum, ≥98.0% (GC) from Sigma-Aldrich , accessed on September 11, 2015 ( PDF ).

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ data sheet 1,5-diazabicyclo [4.3.0] non-5-en, purum, ≥98.0% (GC) from Sigma-Aldrich , accessed on September 11, 2015 ( PDF ).