Tetrahydropyran

This article is about tetrahydropyran, whose IUPAC name is oxane. For ethylene oxide, which has occasionally been named as oxane, see oxirane.
Tetrahydropyran
Tetrahydropyran
Tetrahydropyran
THP
THP
Names
Preferred IUPAC name
Oxane
Other names
Tetrahydropyran,
Oxacyclohexane,
1,5-epoxypentane
Identifiers
3D model (JSmol)
102436
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.005.048 Edit this at Wikidata
EC Number
  • 205-552-8
UNII
  • InChI=1S/C5H10O/c1-2-4-6-5-3-1/h1-5H2 checkY
    Key: DHXVGJBLRPWPCS-UHFFFAOYSA-N checkY
  • InChI=1/C5H10O/c1-2-4-6-5-3-1/h1-5H2
    Key: DHXVGJBLRPWPCS-UHFFFAOYAV
  • O1CCCCC1
Properties
C5H10O
Molar mass 86.134 g·mol−1
Appearance Colourless liquid
Density 0.880 g/cm3
Melting point −45 °C (−49 °F; 228 K)
Boiling point 88 °C (190 °F; 361 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Flammable, Causes skin irritation
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
4
1
Flash point −15.6 °C (3.9 °F; 257.5 K)
Lethal dose or concentration (LD, LC):
3000 mg/kg (oral, rat)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Tetrahydropyran (THP) is the organic compound consisting of a saturated six-membered ring containing five carbon atoms and one oxygen atom. It is named by reference to pyran, which contains two double bonds, and may be produced from it by adding four hydrogens. In 2013, its preferred IUPAC name was established as oxane.[1] The compound is a colourless volatile liquid. Derivatives of tetrahydropyran are, however, more common. 2-Tetrahydropyranyl (THP-) ethers derived from the reaction of alcohols and 3,4-dihydropyran are commonly used as protecting groups in organic synthesis.[2] Furthermore, a tetrahydropyran ring system, i.e., five carbon atoms and an oxygen, is the core of pyranose sugars, such as glucose.

  1. ^ "New IUPAC Organic Nomenclature - Chemical Information BULLETIN" (PDF).
  2. ^ Cite error: The named reference Greene was invoked but never defined (see the help page).