Comprehensive Introduction
3,4-Dihydro-2H-pyran (DHP, CAS 110-87-2) is a six-membered oxygen-containing heterocycle widely used in synthetic organic chemistry as a selective protecting reagent for alcohols. When treated with a catalytic amount of acid, DHP readily reacts with hydroxyl-containing compounds (ROH) to form tetrahydropyranyl (THP) ethers, rendering hydroxyl groups inert under basic or nucleophilic conditions.
This transformation is central to multi-step synthesis of pharmaceuticals, natural products, and functional materials, allowing selective reactivity and preserving sensitive functionalities. DHP-based protection is reversible and clean-THP groups can be smoothly cleaved under mild acidic hydrolysis to regenerate the free alcohol.
Product Details
| Product Name | DHP for Hydroxyl Group Protection |
| CAS NO. | 110-87-2 |
| Synonyms | DHP |
| Molecular Formula | C5H8O |
| HS Code | 2932999099 |
| Structural Formula |  |
Specification
|
Items |
Standard |
|
Appearance |
Colorless transparent liquid |
|
Purity (%) |
≥98.5 |
|
Moisture (%) |
≤0.25 |
|
THP(%) |
1.3 max |
| Density (g/cm³) | 0.922 |
Usage & Core Function of DHP in Alcohol Protection
(A Key Reagent for Hydroxyl Masking in Synthetic Chemistry)
-
Hydroxyl Group Protection via THP Ether Formation:
In the presence of acid (e.g., p-TsOH, HCl), DHP reacts with alcohols to form THP ethers.
This protective group renders hydroxyl groups non-reactive to bases, oxidants, and organometallics.
THP ethers are stable under basic and nucleophilic conditions, making them ideal for complex synthesis workflows.
-
Mild Deprotection:
The THP group is easily removed by mild aqueous acid (e.g., 1% HCl or acetic acid), restoring the original hydroxyl group with high fidelity.
No need for harsh conditions or special reagents.
-
Applications in Multistep Synthesis:
Pharmaceutical synthesis: e.g., steroids, antibiotics, antiretrovirals
Peptide and amino alcohol chemistry
Carbohydrate protection: Selective hydroxyl masking in sugars
Natural product total synthesis
Production Capacity
Full-Cycle Safety Certifications
Recommended Product Applications
- Protecting primary and secondary alcohols in pharmaceutical intermediates
- Synthesis of THP-protected alcohols for drug development
- Total synthesis of complex natural compounds
- Fine chemicals and specialty materials chemistry
- Peptide side chain and carbohydrate hydroxyl protection
Comparison of DHP in Alcohol Protection
|
Parameter |
Lab Grade DHP |
Industrial Grade DHP |
|
Purity (%) |
≥98 |
97–98 |
|
Glycol Impurities |
<0.1% |
0.2–0.5% |
|
Odor |
Mild ether-like |
Stronger odor |
|
Suitability |
Analytical, R&D |
Production-scale use |
|
Heavy Metals |
<1 ppm |
Controlled |
FAQ
Q: Why is DHP used for alcohol protection?
A: DHP forms THP ethers that prevent hydroxyl groups from interfering in synthetic reactions, particularly under basic or nucleophilic conditions.
Q: How do I remove a THP group after protection?
A: Use dilute aqueous acid (e.g., 1% HCl or acetic acid). Deprotection is mild, clean, and efficient.
Q: Can DHP be used for secondary alcohols?
A: Yes, both primary and secondary alcohols react well with DHP to form THP ethers.
Q: Is the protection reversible?
A: Yes, that's one of DHP's key advantages-it offers temporary and selective protection.
Specification
|
Items |
Standard |
|
Appearance |
Colorless transparent liquid |
|
Purity (%) |
≥98.5 |
|
Moisture (%) |
≤0.25 |
|
THP(%) |
1.3 max |
| Density (g/cm³) | 0.922 |
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