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

• CAS: 3001-72-7
• Catalog Number: ACM3001727
• Category: Other Products
• Molecular Weight: 124.18g/mol
• Molecular Formula: C7H12N2
• IUPAC Name: 2,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrimidine
• SMILES: C1CC2=NCCCN2C1
• InChI: InChI=1S/C7H12N2/c1-3-7-8-4-2-6-9(7)5-1/h1-6H2
• InChI Key: SGUVLZREKBPKCE-UHFFFAOYSA-N
• Application: 1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) is a versatile amidine base used in various applications within organic synthesis. Its primary purpose includes facilitating base-mediated reactions such as eliminations, condensations, esterifications, isomerizations, carboxylations, and carbonylations. Additionally, DBN plays a pivotal role in the creation of supertetrahedral chalcogenide clusters and the development of polymer-chalcogenide composite single crystals. As a catalyst, it enhances regioselective Friedel-Crafts C-acylation of pyrroles and serves as a nucleophilic catalyst for the acylation of pyrroles and indoles. Moreover, DBN is employed as a resin curing agent and a catalyst for polyurethanes, highlighting its broad utility in both chemical reactions and industrial applications.
• Complexity: 140
• Covalently-Bonded Unit Count: 1
• Exact Mass: 124.100048g/mol
• Formal Charge: 0
• H-Bond Acceptor: 1
• H-Bond Donor: 0
• Heavy Atom Count: 9
• LogP: -0.17 (LogP)
• Monoisotopic Mass: 124.100048g/mol
• NSC Number: 118106
• Rotatable Bond Count: 0
• UNII: 978M4OL12Q
• XLogP3: -0.2

Synthetic Use

Upstream Synthesis Route 1

• 674303-36-7

• 3001-72-7

Reference: [1] Angewandte Chemie - International Edition, 2004, vol. 43, # 4, p. 478 - 482

Upstream Synthesis Route 2

• 120256-34-0

• 3001-72-7

Reference: [1] Patent: US4892944, 1990, A,

Upstream Synthesis Route 3

• 51333-90-5

• 3001-72-7

Reference: [1]Reppe et al.
[Justus Liebigs Annalen der Chemie, 1955, vol. 596, p. 1,211]

Downstream Synthesis Route 1

• 3001-72-7

• 23159-07-1

Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1984, vol. 38, # 6, p. 526 - 528

Downstream Synthesis Route 2

• 98-54-4
• 3001-72-7
• 616-38-6

• 5396-38-3

Reference: [1]Current Patent Assignee: EVONIK INDUSTRIES AG - US5387718, 1995, A

* For details of the synthesis route, please refer to the original source to ensure accuracy.