2H-Pyran-2-one

Base Information

• Chemical Name: 2H-Pyran-2-one
• CAS No.: 504-31-4
• Molecular Formula: C5H4O2
• Molecular Weight: 96.0856
• Hs Code.: 29322090
• European Community (EC) Number: 207-990-5
• UNII: 8WW45I202V
• DSSTox Substance ID: DTXSID50198441
• Nikkaji Number: J6.216B
• Wikipedia: 2-Pyrone
• Wikidata: Q209475
• Metabolomics Workbench ID: 52207
• ChEMBL ID: CHEMBL1934663
• Mol file: 504-31-4.mol

Synonyms:2-pyrone

Chemical Property of 2H-Pyran-2-one

Chemical Property:

• Appearance/Colour: Clear yellow to brown liquid
• Vapor Pressure: 0.225mmHg at 25°C
• Melting Point: 8-9 °C
• Refractive Index: n20/D 1.53(lit.)
• Boiling Point: 207.5 °C at 760 mmHg
• Flash Point: 89.2 °C
• PSA: 30.21000
• Density: 1.192 g/cm³
• LogP: 0.63980
• Storage Temp.: Refrigerator (+4°C)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 96.021129366
• Heavy Atom Count: 7
• Complexity: 133

Purity/Quality:

98%,99%, ^*data from raw suppliers

α-Pyrone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=O)OC=C1

Technology Process of 2H-Pyran-2-one

There total 32 articles about 2H-Pyran-2-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: 89.0%

5-bromo-5,6-dihydro-2H-pyran-2-one (53646-72-3) → pyran-2-one (504-31-4)

Guidance literature:

With triethylamine; In toluene; at 5 - 40 ℃;

Reference yield: 79.7%

hexane-3,4-cis-diol-2,5-dione (25566-16-9) → pyran-2-one (504-31-4)

Guidance literature:

With sodium dihydrogenphosphate; sodium hydroxide; In acetic acid butyl ester; water; at 80 ℃; for 12h;

Reference yield: 5.0%

3-bromo-2H-pyran-2-one (19978-32-6) + lithium dimethylcuprate (15681-48-8) → 3-methyl-2H-pyran-2-one (31678-73-6) + pyran-2-one (504-31-4)

Guidance literature:

In diethyl ether; at -78 ℃; for 2h; Yields of byproduct given;

DOI:10.1016/0022-328X(85)87397-6

upstream raw materials:

2H-pyran-2-one-6-carboxylic acid

2H-pyran-2-one-5-carboxylic acid

5-bromo-5,6-dihydro-2H-pyran-2-one

5-diazo-1,3-cyclopentadiene

Downstream raw materials:

3-Oxo-2-oxabicylo<2.2.2>oct-7-en-exo-5,exo-6-dicarbonsaeureanhydrid

(1r,2R,3S,4r,5R,6S)-bicyclo<2.2.2>oct-2-ene-2,3,5,6-tetracarboxylic bisanhydride

(Z)-penta-2,4-dienoic acid

naphthalene

Refernces

New synthesis and reactivity of 3-bromoacetyl-4-hydroxy-6-methyl-2H-pyran- 2-one with binucleophilic amines

10.1002/jhet.507

The research investigates the synthesis and reactivity of 3-bromoacetyl-4-hydroxy-6-methyl-2H-pyran-2-one (bromo-DHAA) with various binucleophilic amines. The study begins with the synthesis of bromo-DHAA by reacting dehydroacetic acid (DHAA) with bromine in glacial acetic acid. This compound then reacts with different binucleophilic amines, including alkanediamines, phenylhydrazines, ortho-phenylenediamines, and ortho-aminobenzenethiol, to produce a range of novel heterocyclic products. These products are characterized using IR, 1H and 13C NMR, and mass spectra. The research explores the potential of these compounds for biological activity, with one of the synthesized compounds showing antifungal properties. The study highlights the versatility of bromo-DHAA as a reactive intermediate for generating diverse 2-pyrone derivatives through selective nucleophilic attacks and cyclocondensation reactions.