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

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The correct title of this article is 1,5-Diazabicyclo[4.3.0]non-5-ene. The substitution of any brackets is due to technical restrictions.
1,5-Diazabicyclo[4.3.0]non-5-ene
1,5-Diazabicyclo(4.3.0)non-5-ene
DBN molecule
Names
IUPAC name
2,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrimidine
Other names
DBN
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.019.171 Edit this at Wikidata
  • InChI=1S/C7H12N2/c1-3-7-8-4-2-6-9(7)5-1/h1-6H2 ☒N
    Key: SGUVLZREKBPKCE-UHFFFAOYSA-N ☒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
  • C1CC2=NCCCN2C1
  • [N-]=[N+]3C=1CCCC23CCCC=12
Properties
C7H12N2
Molar mass 124.18 g/mol
Density 1.005 g/cm3
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).
☒N verify (what is checkY☒N ?)

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.

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
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