ChemicalBook > Product Catalog > Pharmaceutical intermediates > Heterocyclic compound > Pyran compounds > Tetrahydro-4H-pyran-4-one
Tetrahydro-4H-pyran-4-one
- Product Name:Tetrahydro-4H-pyran-4-one
- CAS:29943-42-8
- MF:C5H8O2
- MW:100.12
- EINECS:249-967-2
- Mol File:29943-42-8.mol
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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 n
20/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)
- 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
- Language:EnglishProvider:Tetrahydro-4H-pyran-4-one
- Language:EnglishProvider:ACROS
- Language:EnglishProvider:SigmaAldrich
- Language:EnglishProvider:ALFA
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
- Raw materialsEtanolSodium hydroxideHydrochloric acidEthyl acetateDichloromethanePETROLEUM ETHERMagnesium sulfateAcetoneAluminium chlorideDiethyl oxalatePhosphorous acidNickelSodium ethoxideCopperHeptaneSodium dihydrogenorthophosphateDibutyl phthalate ETHYLENE1,2,3,4-Tetrahydronaphthalene3-Chloropropionyl chloride2,2'-Dipyridyl
- Preparation Products4-Aminotetrahydropyran hydrochloride2-(TETRAHYDRO-PYRAN-4-YL)-ETHANOL4-AminotetrahydropyranE-4-Hexen-1-ol
- Tetrahydro-4-pyranol 5-Formylsalicylic acid TETRAHYDRO-2H-PYRAN-4-YLACETYL CHLORIDE TETRAHYDRO-2H-PYRAN-4-CARBOXAMIDE Tetrahydrothiophen-3-one Tetrahydrothiopyran-4-one (2R,3S,5S)-2-Methoxy-3,5-dimethyl-2,3,5,6-tetrahydro-4H-pyran-4-one (2S,3R,5R)-2-Methoxy-3,5-dimethyl-2,3,5,6-tetrahydro-4H-pyran-4-one 6-(2-Pentenyl)-3-(2-pyridinylthio)tetrahydro-2H-pyran-2-one (4R)-4β,5α-Bis(benzyloxy)-6β-(benzyloxymethyl)tetrahydro-2H-pyran-2-one,(4R)-4β,5α-Di(benzyloxy)-6β-(benzyloxymethyl)tetrahydro-2H-pyran-2-one (4R)-4α-Hydroxy-6β-[2-(7-chloro-2-methyl-4-methylnaphthalen-1-yl)ethyl]tetrahydro-2H-pyran-2-one (4S)-4β-Hydroxy-6α-[(E)-2-(p-tolyl)vinyl]tetrahydro-2H-pyran-2-one (2S,3R)-2-Ethoxy-3-methyl-2,3,5,6-tetrahydro-4H-pyran-4-one (2R,5R)-2-Ethoxy-5-methyl-2,3,5,6-tetrahydro-4H-pyran-4-one (2S,3S,5R)-2-Methoxy-3,5-dimethyl-2,3,5,6-tetrahydro-4H-pyran-4-one (3Z)-5-Methyl-5-propyl-3-[[(1R,2R)-3,3-dimethyl-2-(2-methyl-1-propenyl)cyclopropan-1-yl]methylene]tetrahydro-2H-pyran-2-one [2R,(-)]-2,6,6-Trimethyl-2β-vinyl-3,4,5,6-tetrahydro-2H-pyran-5-one (4R)-4α-Hydroxy-6β-[2-(4-bromonaphthalen-1-yl)ethyl]tetrahydro-2H-pyran-2-one
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