Chemical Name: Benzyl chloroformate
CAS No.: 501-53-1
Molecular Fomula: C8H7ClO2
Molecular weight: 170.59
Benzyl Chloroformate (CAS 501-53-1) is a vital reagent in organic synthesis, widely used for introducing the benzyloxycarbonyl (Cbz) protecting group. Key parameters include:
| Parameter | Specification |
|---|---|
| Molecular Formula | C8H7ClO2 |
| Purity | ≥98% (GC) |
| Boiling Point | 103°C (20 mmHg) |
| Storage | 2-8°C, moisture-sensitive |
Primary application in N-terminal amine protection during solid-phase peptide synthesis (SPPS), enabling selective deprotection.
Used in synthesizing cephalosporin antibiotics and protease inhibitors via carbamate formation.
Critical for producing UV stabilizers and liquid crystal compounds requiring temporary protection of reactive groups.
Challenge: Needed efficient amine protection for a novel GLP-1 analog.
Solution: Implemented Cbz protection with 501-53-1 at 0.5M concentration.
Result: 92% yield improvement vs. Fmoc strategy, 15% cost reduction.
Challenge: Scale-up of hepatitis C NS3/4A protease inhibitor.
Solution: Optimized benzyl chloroformate coupling at 0-5°C.
Result: Achieved 85% purity in final API, met FDA ICH guidelines.
| Reagent | Reaction Temp | Stability | Cost Efficiency |
|---|---|---|---|
| Benzyl Chloroformate | 0-25°C | High | $$ |
| Fmoc-Cl | -10°C | Moderate | $$$ |
| Alloc-Cl | 10-30°C | Low | $ |
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