Tetrahydro-4H-pyran-4-one
Description Application- Product Name
- Tetrahydro-4H-pyran-4-one
- CAS No.
- 29943-42-8
- Chemical Name
- Tetrahydro-4H-pyran-4-one
- Synonyms
- dihydro-2H-pyran-4(3H)-one;Oxan-4-one;TETRAHYDROPYRAN-4-ONE;4-THP;4-OXOTETRAHYDROPYRAN;4H-Pyran-4-one, tetrahydro-;EOS-60523;1KG,10KG,25KG;TETRAHYDRO-GAMM;4-Oxacyclohexanone
- CBNumber
- CB3703050
- Molecular Formula
- C5H8O2
- Formula Weight
- 100.12
- MOL File
- 29943-42-8.mol
Tetrahydro-4H-pyran-4-one Property
- 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.
- 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)
Safety
- 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
N-Bromosuccinimide Price
- Product number
- 198242
- Product name
- Tetrahydro-4H-pyran-4-one
- Purity
- 99%
- Packaging
- 1g
- Price
- $43.2
- Updated
- 2025/07/31
- Product number
- 198242
- Product name
- Tetrahydro-4H-pyran-4-one
- Purity
- 99%
- Packaging
- 5g
- Price
- $139
- Updated
- 2025/07/31
- Product number
- T1806
- Product name
- Tetrahydro-4H-pyran-4-one
- Purity
- >95.0%(GC)
- Packaging
- 1g
- Price
- $35
- Updated
- 2025/07/31
- Product number
- T1806
- Product name
- Tetrahydro-4H-pyran-4-one
- Purity
- >95.0%(GC)
- Packaging
- 5g
- Price
- $99
- Updated
- 2025/07/31
- Product number
- T1806
- Product name
- Tetrahydro-4H-pyran-4-one
- Purity
- >95.0%(GC)
- Packaging
- 25g
- Price
- $293
- Updated
- 2025/07/31
Tetrahydro-4H-pyran-4-one Chemical Properties,Usage,Production
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
108-97-4
29943-42-8
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
Tetrahydro-4H-pyran-4-one Preparation Products And Raw materials
Raw materials
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View Lastest Price from Tetrahydro-4H-pyran-4-one manufacturers
- Product
- Tetrahydro-4H-pyran-4-one 29943-42-8
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 99%min
- Supply Ability
- 30tons/month
- Release date
- 2023-02-22
- Product
- Tetrahydro-4H-pyran-4-one 29943-42-8
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 10 mt
- Release date
- 2025-03-10
- Product
- Tetrahydro-4H-pyran-4-one 29943-42-8
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 500000kg
- Release date
- 2024-10-31