1,5-Diazabicyclo[4.3.0]non-5-ene
[CAS# 3001-72-7]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: 1,5-Diazabicyclo[4.3.0]non-5-ene
• Synonyms: DBN
• Molecular Formula: C₇H₁₂N₂
• Molecular Weight: 124.18
• CAS Registry Number: 3001-72-7
• EC Number: 221-087-3
• SMILES: C1CC2=NCCCN2C1

Properties

• Water solubility: soluble
• Density: 1.2±0.1 g/cm³, Calc.^*, 1.005 g/mL (Expl.)
• Index of Refraction: 1.628, Calc.^*
• Boiling Point: 238.3±9.0 °C (760 mmHg), Calc.^*, 95-98 °C (7.5 mmHg) (Expl.)
• Refractive index: 1.519 (Expl.)
• Flash point: 94 °C (Expl.)
• Flash Point: 94.4±0.0 °C, Calc.^*, 94 °C (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H314
• Safety Statements: P280-P305+P351+P338-P310

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

• Transport Information: UN 3267

Discovery and Applications

1,5-Diazabicyclo[4.3.0]non-5-ene, often abbreviated as DBN, is a bicyclic organic compound with the chemical formula C9H12N2. This compound is characterized by a bicyclic structure consisting of a nitrogen atom in each of the two rings, making it a diazabicyclic compound. DBN is primarily known for its strong basicity, which arises from the electron-donating nitrogen atoms present in its structure. The compound has been extensively studied for its reactivity and versatility in various chemical processes.

The discovery of 1,5-diazabicyclo[4.3.0]non-5-ene dates back to the early 20th century, during a period when chemists were exploring bicyclic amines and their potential applications. Early research into DBN focused on understanding its structure, synthesis, and reactivity. It was found that DBN could be synthesized via several synthetic routes, with one of the most common methods involving the reaction of a suitable amine with an alkene. This process leads to the formation of the bicyclic structure, where the nitrogen atoms are incorporated into the rings.

One of the most significant applications of DBN is as a strong base in organic synthesis. Due to its high basicity, DBN is commonly used as a catalyst in a variety of chemical reactions, particularly in the synthesis of complex organic molecules. One of its most notable uses is in the dehydrohalogenation of alkyl halides, where DBN acts as a base to promote the elimination of a halide ion, leading to the formation of an alkene. This reaction is a key step in many synthetic routes, particularly in the production of pharmaceuticals and agrochemicals.

DBN is also used as a catalyst in reactions involving nucleophilic substitution, such as the preparation of amides, esters, and other functionalized compounds. Its ability to activate substrates and facilitate the formation of new carbon-nitrogen or carbon-oxygen bonds makes it an invaluable tool in synthetic chemistry.

In addition to its role as a catalyst in organic synthesis, DBN has found applications in the field of polymer chemistry. It is sometimes used in the polymerization of certain monomers, such as those containing electrophilic groups, where its basicity helps initiate the polymerization process. Furthermore, DBN has been explored for its potential as a catalyst in the synthesis of high-performance polymers, particularly those with unique properties such as high thermal stability or electrical conductivity.

Another area where DBN has been used is in the field of asymmetric synthesis. Researchers have utilized DBN as a chiral catalyst in various enantioselective reactions, such as those involving the synthesis of chiral intermediates for pharmaceutical applications. The strong base properties of DBN, combined with its ability to influence reaction mechanisms, make it a useful tool for creating complex molecules with high stereoselectivity.

In summary, 1,5-diazabicyclo[4.3.0]non-5-ene is a versatile compound with wide-ranging applications in organic synthesis, polymer chemistry, and asymmetric synthesis. Its strong basicity and ability to catalyze important chemical reactions have made it a valuable reagent in the development of new materials and the synthesis of complex organic molecules.

References

2021. Robust superbase-based emerging solvents for highly efficient dissolution of cellulose. Carbohydrate Polymers, 270.
DOI: 10.1016/j.carbpol.2021.118454

1974. Synthesis and antimicrobic properties of 9-alkyl-l,5-diazabicyclo[4.3.0]non-5-enes. Pharmaceutical Chemistry Journal, 8(1).
DOI: 10.1007/bf00757758

2022. Synthetic strategies of pyran derivatives by multicomponent reaction (MCR) approach. Journal of the Iranian Chemical Society, 19(8).
DOI: 10.1007/s13738-022-02581-0