1,8-Diazabicyclo[5.4.0]undec-7-ene
[CAS# 6674-22-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 1,8-Diazabicyclo[5.4.0]undec-7-ene
• Synonyms: 2,3,4,6,7,8,9,10-Octahydropyrimido[1,2-a]azepine; DBU
• Molecular Formula: C₉H₁₆N₂
• Molecular Weight: 152.24
• CAS Registry Number: 6674-22-2
• EC Number: 229-713-7
• SMILES: C1CCC2=NCCCN2CC1

Properties

• Density: 1.019
• Melting point: -70 °C
• Boiling point: 261 °C
• Refractive index: 1.521-1.523
• Flash point: 116 °C
• Water solubility: soluble

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Risk Statements: H290-H301-H302-H312-H314-H318-H412
• Safety Statements: P234-P260-P264-P264+P265-P270-P273-P280-P301+P316-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P362+P364-P363-P390-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	3	H301
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	4	H302
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Acute toxicity	Acute Tox.	4	H312
Skin corrosion	Skin Corr.	1A	H314
Acute toxicity	Acute Tox.	2	H300
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H331
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Carcinogenicity	Carc.	1B	H350
Germ cell mutagenicity	Muta.	2	H341

• Transport Information: UN 3267

Discovery and Applications

1,8-Diazabicyclo[5.4.0]undec-7-ene, commonly known as DBU (Diazabicyclo[5.4.0]undec-7-ene), is a notable chemical compound in organic chemistry with a range of significant applications. This bicyclic diamine, featuring a unique structure, has been utilized in various fields due to its distinctive properties and reactivity.

DBU was first synthesized and characterized in the mid-20th century. Its structure comprises a bicyclic framework with a diazabicyclic ring system, making it a strong base and nucleophile. This structural characteristic contributes to its utility in various chemical reactions and industrial processes.

One of the primary applications of DBU is as a strong, non-nucleophilic base in organic synthesis. Its high basicity allows it to deprotonate weak acids, facilitating various reactions that require strong base conditions. DBU is particularly effective in reactions such as the deprotonation of amides, nitriles, and other functional groups where a strong base is required. This makes it valuable in the synthesis of complex organic molecules and pharmaceuticals.

In addition to its role as a base, DBU is employed as a catalyst in numerous chemical transformations. It serves as an efficient catalyst in the synthesis of heterocyclic compounds, such as pyridines and imidazoles, through processes like cyclization and condensation reactions. Its ability to facilitate these reactions with high selectivity and efficiency enhances its utility in both academic and industrial settings.

DBU's application extends to the field of polymer chemistry, where it is used as a catalyst in the polymerization of various monomers. For example, it is utilized in the ring-opening polymerization of cyclic esters, such as lactones, to produce high-performance polymers with desirable properties. DBU's catalytic activity in these polymerization reactions contributes to the development of advanced materials with specific characteristics.

Another notable application of DBU is in the field of organic electronics. Its strong basicity and ability to interact with different organic compounds make it a suitable candidate for use in the development of organic semiconductors and other electronic materials. DBU's role in these applications involves improving the performance and stability of organic electronic devices.

While DBU offers numerous advantages, its use requires careful handling due to its strong basicity and potential reactivity. Appropriate safety measures should be taken to ensure safe handling and storage, as with other strong bases and reactive chemicals.

References

2021. Reaction screening in multiwell plates: high-throughput optimization of a Buchwald-Hartwig amination. Nature Protocols, 16(2).
DOI: 10.1038/s41596-020-00452-7

2019. Four-component green synthesis of benzochromene derivatives using nano-KF/clinoptilolite as basic catalyst: study of antioxidant activity. Molecular Diversity, 23(1).
DOI: 10.1007/s11030-019-09935-6

2004. Preparation and in vitro synergistic anticancer effect of Vitamin K3 and 1,8-diazabicyclo[5,4,0]undec-7-ene in poly(ethylene glycol)-diacyllipid micelles. International Journal of Pharmaceutics, 271(1-2).
DOI: 10.1016/j.ijpharm.2003.12.011