1,5-Diazabicyclo(4.3.0)non-5-ene

1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) is a chemical compound with the formula C₇H₁₂N₂.[1] It is an amidine base used in organic synthesis. A related compound with related functions is 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The relatively complex nature of the formal names for DBU and DBN (hence the common use of acronyms) reflects the fact that these compounds are bicyclic and contain several functional groups.

1,5-Diazabicyclo[4.3.0]non-5-ene

Names
IUPAC name 2,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrimidine
Other names DBN
Identifiers
CAS Number	3001-72-7
3D model (JSmol)	Interactive image
ChemSpider	68826
ECHA InfoCard	100.019.171
EC Number	221-087-3
PubChem CID	76349
UNII	978M4OL12Q
CompTox Dashboard (EPA)	DTXSID10184087
InChI InChI=1S/C7H12N2/c1-3-7-8-4-2-6-9(7)5-1/h1-6H2 Key: SGUVLZREKBPKCE-UHFFFAOYSA-N InChI=1/C9H12N2/c10-11-8-4-2-6-9(11)5-1-3-7(8)9/h1-6H2 Key: HHCBYVLNFWNEJX-UHFFFAOYAD InChI=1S/C9H12N2/c10-11-8-4-2-6-9(11)5-1-3-7(8)9/h1-6H2 Key: HHCBYVLNFWNEJX-UHFFFAOYSA-N
SMILES C1CC2=NCCCN2C1
Properties
Chemical formula	C7H12N2
Molar mass	124.18 g/mol
Density	1.005 g/cm^3
Boiling point	95 to 98 °C (203 to 208 °F; 368 to 371 K) at 7.5 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

The compounds are employed for dehydrohalogenation[2] reactions as well as base-catalyzed rearrangements.

References

1. Savoca, Ann. C. "1,5-Diazabicyclo[4.3.0]non-5-ene" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289X.rd010.pub2
2. Möller, Fr.; Oediger, H. "1,5-Diazabicyclo[5.4.0]undec-5-ene, a New Hydrogen Halide Acceptor" Angew. Chem. Int. Ed. Engl. , 1967, 5, 76. doi:10.1002/anie.196700761