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| | 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.) | | Fp | 134 °F | | storage temp. | Inert atmosphere,Room Temperature | | form | Liquid | | color | Clear colorless to pale yellow | | Water Solubility | MISCIBLE | | BRN | 106463 | | InChI | 1S/C5H8O2/c6-5-1-3-7-4-2-5/h1-4H2 | | InChIKey | JMJRYTGVHCAYCT-UHFFFAOYSA-N | | SMILES | O=C1CCOCC1 | | CAS DataBase Reference | 29943-42-8(CAS DataBase Reference) | | NIST Chemistry Reference | 4H-Pyran-4-one, tetrahydro-(29943-42-8) |
| 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 | | F | 10 | | Hazard Note | Keep Cold/Flammable/Irritant | | HazardClass | 3.2 | | PackingGroup | III | | HS Code | 29329995 | | Storage Class | 3 - Flammable liquids | | Hazard Classifications | Flam. Liq. 3 |
| | Tetrahydro-4H-pyran-4-one Usage And Synthesis |
| Description | Tetrahydro-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. | | Application | Tetrahydro-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.
| | Chemical Properties | colorless to light yellow liquid | | Uses | Tetrahydro-4-pyrone is used in organic synthesis as building block for more complex chemical structures because it participate in a variety of cycloaddition reactions. | | Synthesis | The general procedure for the synthesis of tetrahydropyranone using pyran-4-one as starting material was as follows: 30 g of intermediate 2 was dissolved in a solvent mixture of 200 mL of toluene and 100 mL of methanol. Subsequently, 3g of 5% Pd/C catalyst was added and the hydrogenation reaction was carried out at room temperature for 5 hours. Upon completion of the reaction, the catalyst was removed by diafiltration and the filtrate was concentrated to dryness. Finally, 26 g of tetrahydropyranone was obtained by distillation purification in 86% yield. | | Purification Methods | Purify 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.] | | References | [1] Patent: CN108586405, 2018, A. Location in patent: Paragraph 0017; 0022
[2] Patent: EP1700853, 2006, A1. Location in patent: Page/Page column 13
[3] Patent: EP1700853, 2006, A1. Location in patent: Page/Page column 14
[4] Chemische Berichte, 1915, vol. 48, p. 684 |
| | Tetrahydro-4H-pyran-4-one Preparation Products And Raw materials |
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