136581
1,5-Diazabicyclo[4.3.0]non-5-ene
98%
Synonym(s):
DBN
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About This Item
Empirical Formula (Hill Notation):
C7H12N2
CAS Number:
Molecular Weight:
124.18
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
EC Number:
221-087-3
Beilstein/REAXYS Number:
2417
MDL number:
Assay:
98%
Form:
liquid
Quality Level
assay
98%
form
liquid
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
General description
DBN is a strong base widely used as a catalyst in organic synthesis to facilitate Michael additions and aldol condensations.
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.
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Danger
hcodes
Hazard Classifications
Skin Corr. 1B
Storage Class
8A - Combustible corrosive hazardous materials
wgk
WGK 3
flash_point_f
201.2 °F - closed cup
flash_point_c
94 °C - closed cup
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
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The simple solvent-free synthesis of 1H-quinazoline-2, 4-diones using supercritical carbon dioxide and catalytic amount of base
Mizuno T, et al.
Tetrahedron Letters, 45(38), 7073-7075 (2004)
Organic base-promoted efficient dehydrogenative/decarboxylative aromatization of tetrahydro-βcarbolines into β-carbolines under air.
Zhao Z, et al.
Tetrahedron Letters, 60(11), 800-804 (2019)
Organic Base-Catalyzed C-S Bond Construction from CO2: A New Route for the Synthesis of Benzothiazolones.
Gao Xiang, et al.
Catalysts, 8(7), 271-271 (2018)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 136581-5G | 04061837670244 |
| 136581-25G | 04061837670237 |
| 136581-100G | 04061838731357 |