| Tetrahydropyran | |
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Oxane |
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Other names
Tetrahydropyran, |
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| Identifiers | |
| CAS number | 142-68-7 |
| PubChem | 8894 |
| ChemSpider | 8554 |
| UNII | V06I3ILG6B |
| DrugBank | DB02412 |
| KEGG | C15345 |
| ChEBI | CHEBI:46941 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C5H10O |
| Molar mass | 86.13 g/mol |
| Density | 0.880 g/cm3 |
| Melting point |
-45 °C, 228 K, -49 °F |
| Boiling point |
88 °C, 361 K, 190 °F |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Tetrahydropyran is the organic compound consisting of a saturated six-membered ring containing five carbon atoms and one oxygen atom. The compound is a colourless volatile liquid, but is obscure. Derivatives of tetrahydropyran are, however, more common. Tetrahydropyranyl (THP-) ethers derived from the reaction of alcohols and dihydropyran are common intermediates in organic synthesis. Furthermore, tetrahydropyran ring system, i.e. a five carbon atoms and an oxygen, is the core of pyranose sugars, such as glucose.
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One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation with Raney nickel of dihydropyran.[1]
In organic synthesis, the 2-tetrahydropyranyl group is used as a protecting group for alcohols.[2][3] Reaction of the alcohol with dihydropyran forms a tetrahydropyranyl ether, protecting the alcohol from a variety of reactions. The alcohol can later be restored readily by acidic hydrolysis with formation of 5-hydroxypentanal.