3,4-Dihydro-2H-pyran-2-methanol
[CAS# 3749-36-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyran compound
• Name: 3,4-Dihydro-2H-pyran-2-methanol
• Synonyms: 2-Hydroxymethyl-3,4-dihydro-2H-pyran; 3,4-Dihydro-2H-pyran-2-ylmethanol; DHP Linker
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.14
• CAS Registry Number: 3749-36-8
• EC Number: 223-150-0
• SMILES: C1CC(OC=C1)CO

Properties

• Density: 1.101
• Boiling point: 92-93 ºC
• Refractive index: 1.478-1.479
• Flash point: 89 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

3,4-Dihydro-2H-pyran-2-methanol is an organic compound with the molecular formula C₆H₈O₃. This colorless liquid, also known by its IUPAC name, 2-methyltetrahydropyran, features a six-membered dihydropyran ring with a hydroxymethyl group attached to the second carbon. Its discovery and utilization are of significant interest in both synthetic organic chemistry and industrial applications due to its versatile reactivity.

The compound was first synthesized in the mid-20th century as part of ongoing research into the chemistry of heterocyclic compounds. The dihydropyran ring system is notable for its presence in various natural products and pharmaceuticals, making derivatives like 3,4-dihydro-2H-pyran-2-methanol valuable in chemical synthesis. The synthesis typically involves the reduction of 2H-pyran-2-carboxaldehyde or related compounds using a suitable reducing agent to yield the desired dihydropyran alcohol.

3,4-Dihydro-2H-pyran-2-methanol is primarily used as an intermediate in organic synthesis. Its utility stems from its ability to undergo various chemical transformations, including esterification, oxidation, and substitution reactions. In particular, the hydroxymethyl group can be readily converted into different functional groups, making this compound a useful building block for the synthesis of more complex molecules.

In the pharmaceutical industry, 3,4-dihydro-2H-pyran-2-methanol serves as a precursor for the development of drugs with diverse biological activities. Its derivatives have been explored for their potential as antiviral, anticancer, and antimicrobial agents. The ability to modify the hydroxymethyl group allows for the creation of compounds with enhanced pharmacological properties.

The compound also finds application in the synthesis of agrochemicals. Its derivatives are used in the production of pesticides and herbicides, where they contribute to the development of molecules with improved efficacy and selectivity. The versatility of the dihydropyran ring system in forming various substituents aids in the creation of agrochemicals tailored to specific agricultural needs.

In addition to its role in pharmaceuticals and agrochemicals, 3,4-dihydro-2H-pyran-2-methanol is used in the synthesis of specialty polymers and materials. The compound can be incorporated into polymerization reactions to create materials with desired properties, such as increased stability or enhanced mechanical performance. This application underscores the compound's importance in materials science and industrial chemistry.

Overall, 3,4-dihydro-2H-pyran-2-methanol is a valuable compound in organic synthesis with broad applications across pharmaceuticals, agrochemicals, and materials science. Its ability to participate in various chemical reactions and its role as a precursor for complex molecules highlight its significance in both research and industrial contexts.

References

2020. Synthesis of pH-degradable polyglycerol-based nanogels by iEDDA-mediated crosslinking for encapsulation of asparaginase using inverse nanoprecipitation. Colloid and Polymer Science, 298(6).
DOI: 10.1007/s00396-020-04675-8

2011. Side Chain Anchoring of Tryptophan to Solid Supports Using a Dihydropyranyl Handle: Synthesis of Brevianamide F. International Journal of Peptide Research and Therapeutics, 17(4).
DOI: 10.1007/s10989-011-9274-8

1999. Development of new dihydropyran linker for solid-phase reaction. Archives of Pharmacal Research, 22(6).
DOI: 10.1007/bf02975331