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Tetrahydro-4H-pyran-4-one

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Tetrahydro-4H-pyran-4-one Basic information
Tetrahydro-4H-pyran-4-one Chemical Properties
  • Boiling point:166-166.5 °C(lit.)
  • Density 1.084 g/mL at 25 °C(lit.)
  • refractive index n20/D 1.452(lit.)
  • Flash point:134 °F
  • storage temp. Keep Cold
  • form Liquid
  • color Clear colorless to pale yellow
  • Water Solubility MISCIBLE
  • BRN 106463
  • InChIKeyJMJRYTGVHCAYCT-UHFFFAOYSA-N
  • CAS DataBase Reference29943-42-8(CAS DataBase Reference)
  • NIST Chemistry Reference4H-Pyran-4-one, tetrahydro-(29943-42-8)
Safety Information
  • Hazard Codes Xi,F
  • Risk Statements 10-36/37/38
  • Safety Statements 24/25-36-26
  • RIDADR UN 1224 3/PG 3
  • WGK Germany 3
  • 10
  • Hazard Note Keep Cold/Flammable/Irritant
  • HazardClass 3.2
  • PackingGroup III
  • HS Code 29329995
MSDS
Tetrahydro-4H-pyran-4-one Usage And Synthesis
  • ApplicationTetrahydro-4-pyrone is used in organic synthesis as a building block for more complex chemical structures because it participates in a variety of cycloaddition reactions. Tetrahydro-4H-pyran-4-one is employed in a study of the enantioselective alpha-aminoxylation of ketones with nitrosobenzene and L-proline in an ionic liquid and it undergoes condensation reactions in the preparation of dipeptides and spiroimidazolones. Tetrahydro-4H-pyran-4-one is also employed in wittig reactions for the synthesis of penicillins and in a ring of vitamin D3. Additionally, tetrahydro-4-pyrone is used as solvents in some reactions.
  • DescriptionTetrahydro-4H-pyran-4-one is used in organic synthesis as building block for more complex chemical structures because it participate in a variety of cycloaddition reactions. Tetrahydro-4H-pyran-4-one is employed in the preparation of 4-methoxytetrahydropyran-4-yl protecting group, synthesis of symmetric tetra substituted methanes. 
    The methyl enol ether is a useful protecting agent for alcohols, e.g. in nucleotide synthesis, with the advantage over 3,4-Dihydro-2H-pyran. Tetrahydro-4H-pyran-4-one is also employed in a study of the enantioselective alpha-aminoxylation of ketones with nitrosobenzene and L-proline in an ionic liquid. It undergoes condensation reactions in the preparation of dipeptides and spiroimidazolones. Tetrahydro-4H-pyran-4-one is also employed in wittig reactions for the synthesis of Penicillins and in a ring of vitamin D3.
  • Chemical Propertiescolorless to light yellow liquid
  • UsesTetrahydro-4-pyrone is used in organic synthesis as building block for more complex chemical structures because it participate in a variety of cycloaddition reactions.
  • Purification MethodsPurify the pyrone by repeated distillation, preferably in a vacuum. [Baker J Chem Soc 296 1944, IR: Olsen & Bredoch Chem Ber 91 1589 1958.] The oxime has m 87-88o and b 110-111o/13mm [Cornubert et al. Bull Soc Chim Fr 36 1950]. The 4-nitrophenylhydrazone forms orange-brown needles from EtOH, m 186o [Cawley & Plant J Chem Soc 1214 1938]. [Beilstein 17 I 131, 17 II 287, 17 III/IV 4171, 17/9 V 21.]
Tetrahydro-4H-pyran-4-one Preparation Products And Raw materials
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