Tetrahydro-4H-pyran-4-one

Base Information

• Chemical Name: Tetrahydro-4H-pyran-4-one
• CAS No.: 29943-42-8
• Molecular Formula: C5H8O2
• Molecular Weight: 100.117
• Hs Code.: 29329995
• European Community (EC) Number: 249-967-2
• DSSTox Substance ID: DTXSID70184048
• Nikkaji Number: J119.557C
• Wikidata: Q72506622
• Mol file: 29943-42-8.mol

Synonyms:Tetrahydro-4H-pyran-4-one;29943-42-8;4-Oxotetrahydropyran;oxan-4-one;DIHYDRO-2H-PYRAN-4(3H)-ONE;tetrahydropyran-4-one;4H-Pyran-4-one, tetrahydro-;143562-54-3;4-thp;MFCD00006581;tetrahydro-2h-pyran-4-one;tetrahydro-pyran-4-one;EINECS 249-967-2;Tetrahydro-.gamma.-pyrone;4-Oxacyclohexanone;Tetrahydro-4-pyrone;Tetrahydropyran-4-on;4-oxo-tetrahydropyran;tetrahydro-4-pyranone;tetrahydro-pyran4-one;tetrahydropyran-4 one;tetrahydro-pyran-4-on;tetrahydro pyran-4-one;dihydro-2H-pyran-4-one;tetrahydro-4H-pyran4-one;tetrahydro4H-pyran-4-one;4-oxotetrahydro-2H-pyrane;terahydro-4H-pyran-4-one;tetrahydo-4H-pyran-4-one;tetrahyro-4H-pyran-4-one;4-TETRAHYDROPYRANONE;SCHEMBL3221;tetrahydro-4H-pyrane-4-one;tetrahydro-4-h-pyran-4-one;dihydro-2H-pyran 4(3H)-one;dihydro-2H-pyran-4 (3H)-one;dihydro-2H-pyran-4-(3H)-one;DTXSID70184048;2,3,5,6-Tetrahydro-4-pyranone;2,3,5,6-tetrahydropyran-4-one;BCP27572;CS-D0601;Tetrahydro-4H-pyran-4-one, 99%;BBL027597;STK505649;AKOS000321371;PB24536;PS-9329;BP-12696;A5539;AM20090400;FT-0601097;T1806;EN300-43315;J-007839;Q-201813;F0001-0924

Chemical Property of Tetrahydro-4H-pyran-4-one

Chemical Property:

• Appearance/Colour: colorless to light yellow liquid
• Vapor Pressure: 1.69mmHg at 25°C
• Refractive Index: n20/D 1.452(lit.)
• Boiling Point: 167.5 °C at 760 mmHg
• Flash Point: 63.6 °C
• PSA: 26.30000
• Density: 1.065 g/cm³
• LogP: 0.36590
• Storage Temp.: Keep Cold
• Water Solubility.: MISCIBLE
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 70.1

Purity/Quality:

98%min ^*data from raw suppliers

Tetrahydro-4-pyrone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, F
• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCC1=O
• 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.
• 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.

Technology Process of Tetrahydro-4H-pyran-4-one

There total 28 articles about Tetrahydro-4H-pyran-4-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.9%

carbon dioxide (124-38-9,18923-20-1) + 3-oxa-1,5-dichloropentane (111-44-4) → Tetrahydro-4H-pyran-4-one (29943-42-8,143562-54-3)

Guidance literature:

With cesium iodide; In ethanol; water; at 90 ℃; under 8250.83 Torr; Temperature; Pressure;

Reference yield: 95.0%

4-nitrosotetrahydro-2H-pyran-4-yl 2,2,2-trichloroacetate (1194657-31-2) → Tetrahydro-4H-pyran-4-one (29943-42-8,143562-54-3) + dinitrogen monoxide (10024-97-2) + trichloroacetic acid (76-03-9)

Guidance literature:

With water; In methanol; aq. phosphate buffer; at 20 ℃; for 24h; pH=7.4; Reagent/catalyst; Kinetics; Sealed tube;

DOI:10.1016/j.bmc.2015.04.023

Reference yield: 92.0%

4-nitrosotetrahydro-2H-pyran-4-yl 2,2-dichloropropanoate → Tetrahydro-4H-pyran-4-one (29943-42-8,143562-54-3) + 2,2-Dichloropropionic acid (75-99-0) + dinitrogen monoxide (10024-97-2)

Guidance literature:

With water; In methanol; aq. phosphate buffer; at 20 ℃; for 24h; pH=7.4; Reagent/catalyst; Kinetics; Sealed tube;

DOI:10.1016/j.bmc.2015.04.023

upstream raw materials:

Tetrahydro-pyran-4-ol

4-pyrone

pent-4-en-2-yn-1-ol

1,5-dimethoxypent-2-yne

Downstream raw materials:

1,6-dioxa-spiro[2.5]octane

oxepan-4-one

4-Pyrrolidino-tetrahydro-4H-pyran-4-carbonitril

4,4-dimethoxytetrahydro-2H-pyran-3-ol