Overview
Di-tert-butyl azodicarboxylate (DBAD) is an organic azo compound primarily used as a dehydrogenation agent in synthetic chemistry. It is a yellow to orange crystalline powder with a molecular weight of 230.26 g/mol. DBAD is highly valued in organic synthesis, particularly in peptide coupling and Mitsunobu reactions, where it facilitates the formation of esters and ethers. DBAD is known for its stability under normal conditions but should be handled with care due to its reactive nature. It is commercially available in various purity grades, with ≥98% purity being the most common for laboratory and industrial use. The compound is typically supplied in sealed containers to prevent degradation from moisture and light.
Physical and Chemical Properties
DBAD is characterized by its bright yellow to orange color and crystalline form. It has a melting point of approximately 90-94°C and is soluble in common organic solvents such as tetrahydrofuran (THF), dichloromethane (DCM), and dimethylformamide (DMF). Its solubility in water is negligible, making it suitable for reactions in non-aqueous environments. The compound is an azo derivative, which means it contains the -N=N- functional group, responsible for its reactivity. DBAD is sensitive to heat, light, and moisture, which can lead to decomposition. Proper storage in a cool, dry, and dark environment is essential to maintain its stability and shelf life.
Main Applications
DBAD is widely used in organic synthesis, particularly in the Mitsunobu reaction, where it serves as an oxidizing agent to convert alcohols into esters or ethers. It is also employed in peptide synthesis for the formation of amide bonds, a critical step in producing peptides and proteins. In addition to these applications, DBAD is utilized in the synthesis of heterocyclic compounds and as a dehydrogenation agent in various chemical transformations. Its versatility and efficiency make it a staple in pharmaceutical and agrochemical research and development.
Safety and Storage
DBAD should be handled with caution due to its potential to cause skin and eye irritation. Personal protective equipment (PPE), including gloves and safety goggles, is recommended when working with this compound. Avoid inhalation of dust and ensure adequate ventilation in the workspace. Storage conditions are critical for maintaining DBAD's stability. It should be kept in a tightly sealed container, away from light, heat, and moisture. Refrigeration is often recommended for long-term storage. In case of spillage, use appropriate absorbent materials and dispose of the waste according to local regulations.
B2B Procurement Guide
When procuring DBAD, it is essential to verify the purity (typically ≥98%) and CAS number (870-50-8) to ensure product authenticity. Reputable suppliers should provide a Certificate of Analysis (COA) detailing the compound's specifications and quality metrics. Bulk purchases may offer cost advantages, but buyers should consider storage limitations and shelf life. For international shipments, ensure compliance with transportation regulations for hazardous materials. Comparing prices from multiple suppliers can help secure competitive rates, but prioritize quality and reliability over cost alone.
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