DHP in Organic Synthesis

DHP in Organic Synthesis

Details
CAS 110-87-2
3,4-Dihydro-2H-pyran (DHP, CAS 110-87-2) is a highly valuable intermediate and reagent in organic synthesis, especially recognized for its role as an alcohol-protecting agent. As a six-membered unsaturated cyclic ether, DHP forms tetrahydropyranyl (THP) ethers when reacted with alcohols under acidic conditions.
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3,4-Dihydro-2H-pyran
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Description
Technical Parameters

Comprehensive Introduction

 

3,4-Dihydro-2H-pyran (DHP, CAS 110-87-2) is a highly valuable intermediate and reagent in organic synthesis, especially recognized for its role as an alcohol-protecting agent. As a six-membered unsaturated cyclic ether, DHP forms tetrahydropyranyl (THP) ethers when reacted with alcohols under acidic conditions. This protection strategy is crucial in multistep synthesis to prevent unwanted reactions at hydroxyl sites while maintaining compatibility with basic and nucleophilic reagents.

 

DHP is a colorless, low-boiling liquid produced via hydrogenation of dihydropyran or renewable furfural. Its reactive vinyl ether structure enables selective modification and controlled transformation of organic molecules, making it indispensable in modern synthetic chemistry labs and pharmaceutical R&D pipelines.

 

Product Details

 

Product Name DHP in organic sythesis CAS 110-87-2
CAS NO. 110-87-2
Synonyms DHP
Molecular Formula C5H8O
HS Code 2932999099
Structural Formula product-152-152

 

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 in Organic Synthesis

 

  • THP Ether Formation (Alcohol Protection):

DHP reacts with primary and secondary alcohols in the presence of an acid catalyst (e.g., p-TsOH, HCl) to form THP ethers. These protect hydroxyl groups from oxidation, acylation, or alkylation in subsequent steps.

 

  • Selective Deprotection:

THP groups are easily removed using mild acid (e.g., acetic acid in water or TFA), providing excellent orthogonality in protecting group strategies.

 

  • Applications in Complex Molecule Synthesis:

Natural products: THP ethers stabilize multifunctional intermediates.

Peptides and carbohydrates: Selective protection of hydroxyl-bearing side chains and sugar alcohols.

API synthesis: Used in drugs like erythromycin, steroids, and alkaloids.

 

  • Stability Advantages:

THP ethers are stable under basic, reductive, and mild oxidative conditions, allowing reactions such as Grignard additions, base-promoted condensations, and metal-catalyzed couplings.

 

Production Capacity

 

34-Dihydro-2H-pyran

 

Full-Cycle Safety Certifications

 

34-Dihydro-2H

 

Recommended Organic Synthesis Applications

 

Multi-step protection of alcohols in natural product total synthesis

Formation of THP ethers in carbohydrate chemistry

Peptide synthesis involving serine, threonine, and tyrosine protection

Grignard and organolithium chemistry involving hydroxyl-containing precursors

Drug intermediate synthesis where hydroxyl masking is critical

 

Packing

 

Available in: 180 kg drums, 1L or 5L glass bottles for laboratory use

 

FAQ

 

Q: Why is DHP preferred for protecting alcohols?

A: It reacts under mild conditions, provides good stability to THP ethers under basic or neutral conditions, and is easily removed when desired.

Q: Is DHP suitable for automated synthesis workflows?

A: Yes. Its predictable behavior and compatibility with standard protection-deprotection protocols make it ideal for automated and high-throughput synthesis.

Q: Can DHP be used in scale-up processes?

A: Absolutely. DHP is available in bulk and is used in kilogram-to-ton scale in pharmaceutical and fine chemical industries.

 

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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