Chemical Information:
- IUPAC Name: O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate
- Common Name: HBTU
- CAS Number: 94790-37-1
- Molecular Formula: C₁₀H₁₆F₆N₅OP
- Molecular Weight: 379.23 g/mol
Structure and Properties:
- Chemical Structure: HBTU consists of a tetramethyluronium group bond to a benzotriazole ring, with a hexafluorophosphate counterion. Its structure is often depicted as
- Appearance: It is typically a white to off-white crystalline powder.
- Solubility: Soluble in organic solvents such as dimethylformamide (DMF), dimethyl sulfoxide (DMSO), and acetonitrile (ACN).
Chemical Behavior:
- Reactivity: HBTU is a highly efficient coupling reagent used in peptide synthesis. It facilitates the formation of amide bonds by activating carboxylic acids, making them more reactive towards nucleophilic attack by amines.
- Stability: HBTU is relatively stable but should be store in a cool, dry place away from light and moisture to maintain its reactivity.
Applications:
- Peptide Synthesis: HBTU is widely used in solid-phase peptide synthesis (SPPS) and solution-phase peptide synthesis due to its high efficiency and low racemization rates. It provides faster reaction times and higher yields compared to other coupling reagents.
- Amide Bond Formation: It is employ in the synthesis of amides, esters, and other derivatives in organic chemistry. Its high reactivity and selectivity make it a preferr reagent for complex molecule construction.
- Drug Development: HBTU is used in the pharmaceutical industry for the synthesis of peptide-based drugs and other bioactive molecules. Its ability to form stable and high-purity peptides is critical in drug design and development.
Safety and Handling:
- Hazards: HBTU is an irritant and can cause skin and eye irritation upon contact. Inhalation of dust can cause respiratory tract irritation.
- Protective Measures: Use appropriate personal protective equipment (PPE) such as gloves, safety goggles, and lab coats. Work with HBTU should be conduct in a well-ventilated area, preferably in a fume hood.
- Storage: Store in tightly sealed containers, away from light, moisture, and incompatible substances such as strong oxidizing agents.
Environmental Impact:
- Degradation: HBTU is generally not considered to be highly hazardous to the environment, but care should be taken to avoid significant releases.
- Disposal: Disposal of HBTU must be carried out in accordance with local regulations, typically requiring containment and disposal as hazardous waste.
Regulatory Information:
- Regulatory Status: HBTU is subject to regulations regarding its handling, storage, and disposal due to its hazardous nature. It is classified as a hazardous substance under various national and international guidelines.
Conclusion
By understanding the chemical properties, applications, and safety measures associated with HBTU, researchers and industry professionals can effectively utilize this powerful coupling reagent in various scientific and industrial processes while ensuring safety and regulatory compliance.