1,5-Diazabicyclo[4.3.0]non-5-ene/octanoic acid salt
[CAS# 226093-04-5]

Identification

• Classification: Catalysts and additives
• Name: 1,5-Diazabicyclo[4.3.0]non-5-ene/octanoic acid salt
• Molecular Formula: C₁₅H₂₈N₂O₂
• Molecular Weight: 268.40
• CAS Registry Number: 226093-04-5
• SMILES: C1CCN=C2CCCN12.C(CCCC)(CC)C(=O)O

Discovory and Applicatios

1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) octanoic acid salt is a chemical compound that has been developed to combine the characteristics of a strong non-nucleophilic organic base with the beneficial properties of an organic acid salt. The compound emerged from the exploration of bicyclic amidine structures, such as DBN, in the mid-20th century when researchers were investigating new catalysts and bases for use in organic synthesis. DBN itself was known for its strong basicity and efficiency in promoting various chemical reactions. By combining it with octanoic acid, a fatty acid, the result is a salt form that is both versatile and more manageable in terms of solubility and handling.

The DBN/octanoic acid salt finds its primary application in organic synthesis, especially in reactions requiring a strong, non-nucleophilic base. Its strong basicity allows it to effectively deprotonate weak acids or serve as a catalyst in condensation reactions, aldol reactions, and other transformations where a basic environment is required. The octanoic acid component of the salt helps to improve its solubility in organic solvents, making it a more efficient base in reactions involving hydrophobic or non-polar compounds. This enhanced solubility also facilitates easier product separation and purification.

In polymer chemistry, DBN/octanoic acid salt has been utilized as a catalyst in the production of polyurethanes. The base plays a critical role in facilitating the isocyanate-polyol reaction, which forms the backbone of polyurethane materials. The controlled reactivity offered by the salt form allows for fine-tuning of reaction conditions, enabling more precise control over polymer properties such as elasticity, hardness, and thermal stability.

Another important application of the DBN/octanoic acid salt is in pharmaceutical synthesis. Its role as a base in peptide coupling reactions is significant, especially in the formation of amide bonds. The salt's strong base properties help to promote the coupling process, ensuring efficient and clean synthesis of peptides, which are essential in drug development and research. Additionally, DBN/octanoic acid salt has been employed in the synthesis of various drug intermediates, offering benefits in terms of reaction selectivity and yield.

The compound is also used in green chemistry applications due to its ability to function effectively under mild reaction conditions. This reduces the need for harsh reagents or extreme temperatures, making it an attractive choice for environmentally friendly chemical processes. The fatty acid salt component provides additional benefits in terms of biodegradability, further aligning the compound with sustainable chemistry practices.

Despite its utility, DBN/octanoic acid salt must be handled carefully due to its strong basicity, which can pose risks to human health if not managed properly. Appropriate safety measures, including the use of gloves and protective eyewear, are recommended when working with this compound in laboratory or industrial settings.