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136581 Sigma-Aldrich

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

98%

Synonym: DBN

  • CAS Number 3001-72-7

  • Empirical Formula (Hill Notation) C7H12N2

  • Molecular Weight 124.18

  •  Beilstein/REAXYS Number 2417

  •  EC Number 221-087-3

  •  MDL number MFCD00005554

  •  PubChem Substance ID 24848287

  •  NACRES NA.22

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Properties

Related Categories Acids & Bases, Bases, Chemical Synthesis, Organic Bases, Synthetic Reagents More...
assay   98%
refractive index   n20/D 1.519 (lit.)
bp   95-98 °C/7.5 mmHg (lit.)
density   1.005 g/mL at 25 °C (lit.)
SMILES string   C1CN=C2CCCN2C1
InChI   1S/C7H12N2/c1-3-7-8-4-2-6-9(7)5-1/h1-6H2
InChI key   SGUVLZREKBPKCE-UHFFFAOYSA-N

Description

Application

1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) can be used as:      
•   A reagent for the synthesis of β-carbolines from tetrahydro-β-carbolines via dehydrogenative/decarboxylative aromatization.       
•  A nucleophilic organocatalyst in the regioselective C-acylation of pyrroles and indoles by Friedel−Crafts acylation reaction.
•   A superbase in the formulation of a ternary liquid-liquid phase changing system, along with hexadecane and hexanol, to capture hydrogen sulfide gas.      
•  A base for the preparation of 1H-quinazoline-2,4-diones from 2-aminobenzonitriles using supercritical carbon dioxide as a reactant and a solvent.
•   A catalyst for the synthesis of benzothiazolones by the reaction between 2-aminothiophenols and CO2 by cyclocarbonylation reaction via C-S bond formation.

Packaging

5, 25, 100 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS05  GHS05
Signal word 
Danger
Hazard statements 
RIDADR 
UN 3267 8 / PGII
WGK Germany 
WGK 3
Flash Point(F) 
201.2 °F - closed cup
Flash Point(C) 
94 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

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Peer-Reviewed Papers
15

References

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