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

1,5-Diazabicyclo[4.3.0]non-5-ene
1,5-Diazabicyclo(4.3.0)non-5-ene
DBN molecule
Names
Preferred 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
EC Number
  • 221-087-3
UNII
  • 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
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).
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Infobox references

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.

The acetate salt is a room-temperature ionic liquid used for processing cellulose fibers by acting as a replacement for the unstable N-Methylmorpholine N-oxide used for making lyocell.[3][4]

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
  3. ^ Zhang, Jinming; Wu, Jin; Yu, Jian; Zhang, Xiaoyu; He, Jiasong; Zhang, Jun. "Application of ionic liquids for dissolving cellulose and fabricating cellulose-based materials: state of the art and future trends." Mat. Chem. Front. 2017, 1 (7), 1273-90. doi:10.1039/C6QM00348F
  4. ^ Ioncell - Enter the new era of textile production!