| Identification | More | [Name]
Tetrahydro-4H-pyran-4-one | [CAS]
29943-42-8 | [Synonyms]
4-OXOTETRAHYDROPYRAN
4-THP
TETRAHYDRO-2H-PYRAN-4-ONE
TETRAHYDRO-4H-PYRAN-4-ONE
TETRAHYDRO-GAMMA-PYRONE
TETRAHYDROPYRAN-4-ONE
2,3,5,6-Tetrahydro-4-pyranone
4-Oxacyclohexanone
Tetrahydro-4-pyrone
TetrahydroHpyranone
Tetrahydropyran-4-on
Tetrahydro-4H-pyran-4-one,98%
Tetrahydo-4H-pyran-4-one
4H-Pyran-4-one, tetrahydro-
Tetrahydro-4H-pyran-4-one 97%
Tetranydropyran-4-one
Tetrahydro-4-H-prran-one
4-Oxotetrahydopyran
2,3,5,6-Tetrahydropyran-4-one
3,5,6-Trihydro-2H-pyran-4-one | [EINECS(EC#)]
249-967-2 | [Molecular Formula]
C5H8O2 | [MDL Number]
MFCD00006581 | [Molecular Weight]
100.12 | [MOL File]
29943-42-8.mol |
| Chemical Properties | Back Directory | [Appearance]
colorless to light yellow liquid | [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. ]
Keep Cold | [form ]
Liquid | [color ]
Clear colorless to pale yellow | [Water Solubility ]
MISCIBLE | [Detection Methods]
GC,NMR | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,F | [Risk Statements ]
R10:Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [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 |
| Questions And Answer | Back Directory | [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.
|
| Hazard Information | Back Directory | [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] Patent: EP1700853, 2006, A1. Location in patent: Page/Page column 14
[5] Chemische Berichte, 1915, vol. 48, p. 684 |
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