1,8-Diazabicyclo[5.4.0]-7-undecene 2-ethylhexoate
[CAS# 33918-18-2]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: 1,8-Diazabicyclo[5.4.0]-7-undecene 2-ethylhexoate
• Synonyms: 2-ethylhexanoic acid;2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine
• Molecular Formula: C₉H₁₆N₂^.C₈H₁₆O₂
• Molecular Weight: 296.45
• CAS Registry Number: 33918-18-2
• EC Number: 608-915-2
• SMILES: CCCCC(CC)C(=O)O.C1CCC2=NCCCN2CC1

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H302-H314-H317-H318
• Precautionary Statements: P260-P261-P264-P264+P265-P270-P272-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P333+P317-P362+P364-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318

Discovory and Applicatios

1,8-Diazabicyclo[5.4.0]-7-undecene 2-ethylhexoate is a specialized chemical compound known for its use as a strong, non-nucleophilic base in various organic synthesis processes. This compound, commonly abbreviated as DBU 2-ethylhexoate, is derived from the bicyclic guanidine structure of DBU, combined with 2-ethylhexoic acid. The compound was discovered during efforts to enhance the performance and versatility of bases used in industrial-scale chemical reactions.

The discovery of 1,8-diazabicyclo[5.4.0]-7-undecene 2-ethylhexoate stems from a need to develop more efficient catalysts and reaction promoters that are capable of functioning under a wide range of conditions. Traditional bases often pose limitations in terms of reactivity, solvent compatibility, or thermal stability, which can hinder large-scale applications. The combination of DBU with 2-ethylhexoic acid helped overcome these issues, producing a compound with improved solubility, better control over reactivity, and enhanced performance in industrial reactions.

One of the primary applications of 1,8-diazabicyclo[5.4.0]-7-undecene 2-ethylhexoate is in the polymer industry, particularly in the production of polyurethane foams. It serves as a catalyst that accelerates the polymerization process, allowing for more efficient production cycles and better control over the properties of the resulting materials. The compound is also used in the curing processes of epoxy resins, improving their hardness and thermal stability.

In addition to its role in polymer chemistry, 1,8-diazabicyclo[5.4.0]-7-undecene 2-ethylhexoate is utilized in various organic reactions, such as alkylations, acylations, and transesterifications. Its strong basicity, combined with its ability to remain stable in both polar and non-polar solvents, makes it highly versatile for a wide range of synthetic applications. Furthermore, the compound is valued for its selectivity, reducing the formation of undesired side products during complex chemical transformations.

The versatility of 1,8-diazabicyclo[5.4.0]-7-undecene 2-ethylhexoate extends to applications in coatings and adhesives, where it functions as a catalyst in the formulation of specialty materials. Its ability to promote fast curing and cross-linking reactions is essential for creating durable, high-performance coatings that can withstand harsh environmental conditions. Similarly, in adhesives, the compound enhances bonding strength and thermal resistance.

Overall, 1,8-diazabicyclo[5.4.0]-7-undecene 2-ethylhexoate has established itself as a valuable component in industrial chemical processes due to its robust basicity, stability, and compatibility with a broad range of applications.