1-Hydroxy-7-azabenzotriazole CAS 39968-33-7

Chemical Name: 1-Hydroxy-7-azabenzotriazole
CAS No.: 39968-33-7
Molecular Fomula: C5H4N4O
Molecular weight: 136.11
Appearance: white powder
Assay: ≥98.0%

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Table of Contents

1-Hydroxy-7-azabenzotriazole (HOAt) CAS 39968-33-7: Technical Specifications

Core Parameters

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

Structural Advantages

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.

2. Industrial Applications of HOAt

Pharmaceutical Synthesis

As critical component in SPPS (Solid Phase Peptide Synthesis):

  • Reduces racemization to <0.5% in β-lactam antibiotics production
  • Enables high-yield (>85%) coupling in oligonucleotide synthesis
  • Essential for macrocyclization in HCV protease inhibitors

Advanced Material Science

• 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

3. Operational Protocols

Recommended Workflow

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)

Safety Handling

• PPE Requirements: Nitrile gloves, chemical goggles
• Storage: -20°C under argon atmosphere
• Shelf Life: 24 months in original packaging

4. Technical Implementation Cases

Case 1: Antiviral Drug Intermediate Synthesis

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%

Case 2: High-Throughput Peptide Library

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

5. Verified Client Implementations

Pharmaceutical Manufacturer A (Germany)

• Application: Continuous production of GLP-1 analogs
• Volume: 120kg/month HOAt consumption
• Benefit: Reduced cycle time by 40% vs HOBt protocol

Research Institute B (Japan)

• Project: Development of antimicrobial peptidomimetics
• Usage: 5g-10kg scale over 18 months
• Achievement: 7 patent filings enabled by HOAt chemistry

6. Technical Support & Ordering

Contact Our Chemistry Team

For analytical reports, bulk pricing (25kg+ drums), or custom synthesis inquiries:
Email: info@vivalr.com
Tel: (86) 15866781826
Office Hours: GMT+8 08:30-17:30

Sample Request Form

[Company Name]: ___________
[Application]: _______________
[Required Purity]: _________
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