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4H-PYRAN-4-ONE

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CAS:108-97-4
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4H-PYRAN-4-ONE Basic information
Product Name:4H-PYRAN-4-ONE
Synonyms:4H-PYRAN-4-ONE;GAMMA-PYRONE;GAMMA-PYRONE, 4-PYRONE;PYRAN-4-ONE;4H-Pyran, 4-oxo-;4H-PYRAN-4-ONE, 98+%;4-Pyrone;Pyrocoman
CAS:108-97-4
MF:C5H4O2
MW:96.08
EINECS:203-634-8
Product Categories:
Mol File:108-97-4.mol
4H-PYRAN-4-ONE Structure
4H-PYRAN-4-ONE Chemical Properties
Melting point 32-34 °C(lit.)
Boiling point 210-215 °C(lit.)
density 1.20
refractive index 1.5238
Fp 214 °F
storage temp. 2-8°C
solubility Slightly soluble in water, soluble in alcohol and oils.
form clear liquid
color Light yellow to Brown
OdorWarm, slight ly pungent, hay-like herbaceous odor of moderate to poor tenacity.
BRN 105293
Stability:Polymerizes under exposure to air (oxygen) and alkali. Turns darker brown, and its odor fades.
InChI1S/C5H4O2/c6-5-1-3-7-4-2-5/h1-4H
InChIKeyCVQUWLDCFXOXEN-UHFFFAOYSA-N
SMILESO=C1C=COC=C1
LogP-0.628 (est)
CAS DataBase Reference108-97-4
Safety Information
Safety Statements 22-24/25
WGK Germany 3
3-8-10
HS Code 2932.99.9090
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
SigmaAldrich English
4H-PYRAN-4-ONE Usage And Synthesis
Uses4H-Pyran-4-one was used in the synthesis of probes grafted on the lipid headgroups.
Preparation1) from Diethylacetone dioxalate by cyclization to Chelidonic acid (gamma-Pyrone- 2,6-dicarboxylic acid). The acid yields 4H-Pyran-4-one by decarboxylation.
2) by heating of I-Methoxypent-l -en-3-yn-5- al diethylacetal with Methanol and water, using Mercuric sulfate or Sulfuric acid catalyst.
DefinitionChEBI: A pyranone that is 4H-pyran substituted by an oxo group at position 4.
Synthesis
3-Pentanone, 1,1,5,5-tetramethoxy-

159015-78-8

4H-PYRAN-4-ONE

108-97-4

Example 1 (Synthesis of pyran-4-one): In a 10 mL glass reaction flask fitted with a stirring device and a dropping funnel, 1.0 g (4.8 mmol) of 1,1,5,5-tetramethoxypentan-3-one (CAS: 159015-78-8) was added. Under cooling in an ice bath, 1.2 mL (14.1 mmol) of 12 mol/L hydrochloric acid solution was slowly added dropwise to the reaction flask. After the dropwise addition, the reaction mixture was stirred at room temperature for 4 hours. Upon completion of the reaction, the reaction solution was analyzed by gas chromatography (internal standard method) to confirm the formation of 0.45 g (yield: 97%) of pyran-4-one.

Purification MethodsPurify -pyrone by vacuum distillation; the distillate crystallises and is hygroscopic. It is non-steam vola
References[1] Patent: EP1700853, 2006, A1. Location in patent: Page/Page column 12
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