136581

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

98%

• Synonym(s): DBN
• Empirical Formula (Hill Notation): C₇H₁₂N₂
• CAS Number: 3001-72-7
• Molecular Weight: 124.18
• Beilstein: 2417
• EC Number: 221-087-3
• MDL number: MFCD00005554
• UNSPSC Code: 12352005
• PubChem Substance ID: 24848287
• NACRES: NA.22

Properties

• 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

Description

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.

Safety Information

• Pictograms: GHS05
• Signal Word: Danger
• Hazard Statements: H314
• Precautionary Statements: P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363 - P405
• Hazard Classifications: Skin Corr. 1B
• Storage Class Code: 8A - Combustible corrosive hazardous materials
• WGK: WGK 3
• Flash Point(F): 201.2 °F - closed cup
• Flash Point(C): 94 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves