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136581

Sigma-Aldrich

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

98%

Sinonimo/i:

DBN

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About This Item

Formula empirica (notazione di Hill):
C7H12N2
Numero CAS:
3001-72-7
Peso molecolare:
124.18
Beilstein:
2417
Numero CE:
221-087-3
Numero MDL:
MFCD00005554
Codice UNSPSC:
12352005
ID PubChem:
24848287
NACRES:
NA.22

Livello qualitativo

200

Saggio

98%

Forma fisica

liquid

Indice di rifrazione

n20/D 1.519 (lit.)

P. eboll.

95-98 °C/7.5 mmHg (lit.)

Densità

1.005 g/mL at 25 °C (lit.)

Stringa SMILE

C1CN=C2CCCN2C1

InChI

1S/C7H12N2/c1-3-7-8-4-2-6-9(7)5-1/h1-6H2
SGUVLZREKBPKCE-UHFFFAOYSA-N

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Descrizione generale

DBN is a strong base widely used as a catalyst in organic synthesis to facilitate Michael additions and aldol condensations.

Applicazioni

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.

Pittogrammi

Corrosion
GHS05

Avvertenze

Danger

Indicazioni di pericolo

H314

Classi di pericolo

Skin Corr. 1B

Codice della classe di stoccaggio

8A - Combustible corrosive hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

201.2 °F - closed cup

Punto d’infiammabilità (°C)

94 °C - closed cup

Dispositivi di protezione individuale

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificati d'analisi (COA)

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Organic base-promoted efficient dehydrogenative/decarboxylative aromatization of tetrahydro-βcarbolines into β-carbolines under air.
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Tetrahedron Letters, 60(11), 800-804 (2019)
The simple solvent-free synthesis of 1H-quinazoline-2, 4-diones using supercritical carbon dioxide and catalytic amount of base
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Tetrahedron Letters, 45(38), 7073-7075 (2004)
Organic Base-Catalyzed C-S Bond Construction from CO2: A New Route for the Synthesis of Benzothiazolones.
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Catalysts, 8(7), 271-271 (2018)
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