Chemical Information :
- IUPAC Name: O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate
- Common Name: HATU
- CAS Number: 148893-10-1
- Molecular Formula: C₈H₁₆F₆N₄OP
- Molecular Weight: 380.21 g/mol
Structure and Properties:
- Chemical Structure: HATU consists of a tetramethyluronium group bond to an azabenzotriazole ring, with a hexafluorophosphate counterion. Its structure is often depict 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: HATU 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: HATU is relatively stable but should be stor in a cool, dry place away from light and moisture to maintain its reactivity.
Applications:
- Peptide Synthesis: HATU 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: HATU is used in the pharmaceutical industry for the synthesis of peptide-bas 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: HATU 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 HATU should be conduct in a well-ventilat 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: HATU is generally not considered to be highly hazardous to the environment, but care should be taken to avoid significant releases.
- Disposal: Disposal of HATU must be carried out in accordance with local regulations, typically requiring containment and disposal as hazardous waste.
Regulatory Information:
- Regulatory Status: HATU is subject to regulations regarding its handling, storage, and disposal due to its hazardous nature. It is classifi as a hazardous substance under various national and international guidelines.