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

Base Information

• Chemical Name: 1,5-Diazabicyclo[4.3.0]non-5-ene
• CAS No.: 3001-72-7
• Molecular Formula: C7H12N2
• Molecular Weight: 124.186
• Hs Code.: 2933.59
• European Community (EC) Number: 221-087-3
• NSC Number: 118106
• UNII: 978M4OL12Q
• DSSTox Substance ID: DTXSID10184087
• Nikkaji Number: J151.114I
• Wikipedia: 1,5-Diazabicyclo(4.3.0)non-5-ene
• Wikidata: Q307070
• ChEMBL ID: CHEMBL3303308
• Mol file: 3001-72-7.mol

Synonyms:1,5-diazabicyclo(4.3.0)non-5-ene;1,5-diazabicyclo(4.3.0)non-5-ene monofumarate;2,3,4,6,7,8-hexahydropyrrolo(1,2-a)pyrimidine;diazabicyclo(4.3.0)nonen;diazabicyclo(4.3.0)nonene

Chemical Property of 1,5-Diazabicyclo[4.3.0]non-5-ene

Chemical Property:

• Appearance/Colour: clear colorless to yellowish liquid
• Refractive Index: n20/D 1.519(lit.)
• Boiling Point: 238.3 °C at 760 mmHg
• PKA: 13.42±0.20(Predicted)
• Flash Point: 97.9 °C
• PSA: 15.60000
• Density: 1.2 g/cm³
• LogP: 0.25790
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: soluble
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 124.100048391
• Heavy Atom Count: 9
• Complexity: 140

Purity/Quality:

99% ^*data from raw suppliers

1,5-Diazabicyclo[4.3.0]non-5-ene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC2=NCCCN2C1
• Description: 1,5-Diazabicyclo [4.3.0]non-5-ene is a amidine base used in organic synthesis. It is employed for dehydrohalogenation reactions as well as base-catalyzed rearrangements. It can also be used as the nucleophilic catalyst for the Friedel-Crafts acylation of pyrroles and indoles2. Further, it is used as a resin curing agent and polyurethane catalyst.
• Uses: 1,5-Diazabicyclo[4.3.0]non-5-ene is employed for dehydrohalogenation reactions and base-catalyzed rearrangements in organic synthesis. It is an amidine base used in organic synthesis. Further, it is used as a resin curing agent and polyurethane catalyst. 1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) is an amidine base commonly used in the base-mediated eliminations, condensations, esterifications, isomerizations, carboxylations and carbonylations.It is used in the preparation of supertetrahedral chalcogenide clusters and single crystals of polymer-chalcogenide composites.It also acts as a catalyst for the regioselective Friedel-Crafts C-acylation of pyrroles.

Technology Process of 1,5-Diazabicyclo[4.3.0]non-5-ene

There total 12 articles about 1,5-Diazabicyclo[4.3.0]non-5-ene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

1-(3-azidopropyl)pyrrolidin-2-one (674303-36-7) → DBN (3001-72-7)

Guidance literature:

1-(3-azidopropyl)pyrrolidin-2-one; With oxalyl dichloride; In dichloromethane; at 0 - 25 ℃; for 25h;

With amberlite IRA 400 (OH(-)); In methanol;

DOI:10.1002/anie.200352750

Reference yield: 66.7%

1-methyl-1-azonia-5-azabicyclo[4,3,0]-5-nonene methyl carbonate (120256-34-0) → DBN (3001-72-7)

Guidance literature:

Reference yield:

2,3,4,6,7,8-hexahydro-1H-pyrrolo[1,2-a]pyrimidin-5-ylium; bromide → DBN (3001-72-7)

Guidance literature:

With amberlite IRA 400 (OH(-)); In methanol;

DOI:10.1002/anie.200352750

upstream raw materials:

3-(2-oxopyrrolidin-1-yl)propanenitrile

3-<(3-cyanopropyl)amino>propylamine

1-(3-azidopropyl)pyrrolidin-2-one

1-(2-chloro-ethyl)-pyrrolidin-2-one

Downstream raw materials:

diethyl 4-(allylethylamino)benzylacetamidomalonate

C₁₈H₃₀N₄O₂

1-phenyl-2,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrimidin-1-ium bis(trifluoromethylsulfonyl)imide

1-(3-aminopropyl)-2-pyrrolidone

Refernces

• 1、 Arimitsu, Koji,Endo, Ryosuke. "Application to photoreactive materials of photochemical generation of superbases with high efficiency based on photodecarboxylation reactions". . p. 4461 - 4463. Retrieved 2014/01/06.
• 2、 Baidya,Mayr, Herbert. "Nucleophilicities and carbon basicities of DBU and DBN". . p. 1792 - 1794. Retrieved 2008/12/22.