Chemical Name: 1-Hydroxy-7-azabenzotriazole
CAS No.: 39968-33-7
Molecular Fomula: C5H4N4O
Molecular weight: 136.11
Appearance: white powder
Assay: ≥98.0%
Parameter | HOAt Specification | HOBt Comparison | EDC·HCl Comparison |
---|---|---|---|
Molecular Formula | C6H5N4O | C6H5N3O | C8H17N3·HCl |
Molecular Weight | 148.13 g/mol | 135.12 g/mol | 191.70 g/mol |
Appearance | White crystalline powder | Off-white powder | White crystalline |
Solubility | DMSO, DMF (>50 mg/mL) | Limited in DCM | Water soluble |
Optimal pH Range | 4.5-6.5 (peptide synthesis) | 5.0-7.0 | 4.0-6.5 |
HOAt's nitrogen-rich bicyclic structure enables superior activation of carboxyl groups compared to traditional coupling agents. The 7-aza modification enhances nucleophilicity while maintaining thermal stability up to 150°C.
As critical component in SPPS (Solid Phase Peptide Synthesis):
• Corrosion inhibition efficiency: 92-95% in acidic media (pH 2-4)
• Photostabilizer in polymer films: extends UV resistance by 3-5X
• Chelating agent for transition metals in catalytic systems
1. Dissolve in anhydrous DMF (0.4M concentration)
2. Molar ratio: 1.2 equiv relative to limiting reagent
3. Maintain reaction temperature at 0-5°C during activation
4. Monitor by HPLC (retention time: 3.2-3.5 min)
• PPE Requirements: Nitrile gloves, chemical goggles
• Storage: -20°C under argon atmosphere
• Shelf Life: 24 months in original packaging
Client: EU-based CDMO
Challenge: Achieve >90% yield in 32-membered macrocycle formation
Solution: HOAt/HATU system at 0.1M scale
Outcome: 92% isolated yield, reduced dimerization to <2%
Client: US Biotech Startup
Issue: Coupling efficiency drop after 15-mer length
Resolution: HOAt/DIEA in continuous flow reactor
Result: Successful synthesis of 45-mer peptide with 88% purity
• Application: Continuous production of GLP-1 analogs
• Volume: 120kg/month HOAt consumption
• Benefit: Reduced cycle time by 40% vs HOBt protocol
• Project: Development of antimicrobial peptidomimetics
• Usage: 5g-10kg scale over 18 months
• Achievement: 7 patent filings enabled by HOAt chemistry
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