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Tetrahydro-4H-pyran-4-one

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Tetrahydro-4H-pyran-4-one Basic information

Product Name:
Tetrahydro-4H-pyran-4-one
Synonyms:
  • Tetrahydro-4-pyrone
  • TETRAHYDRO-GAMMA-PYRONE
  • TETRAHYDROPYRAN-4-ONE
  • TETRAHYDRO-4H-PYRAN-4-ONE
  • TETRAHYDRO-2H-PYRAN-4-ONE
  • TetrahydroHpyranone
  • 4-OXOTETRAHYDROPYRAN
  • 4-THP
CAS:
29943-42-8
MF:
C5H8O2
MW:
100.12
EINECS:
249-967-2
Product Categories:
  • blocks
  • Oxygen cyclic compounds
  • Carbonyl Compounds
  • Pyrans, Piperidines &Piperazines
  • Ketone
  • Pyrans, Piperidines & Piperazines
  • Heterocycles
  • Heterocycles series
  • Heterocycle-other series
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 
n20/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
InChIKey
JMJRYTGVHCAYCT-UHFFFAOYSA-N
CAS DataBase Reference
29943-42-8(CAS DataBase Reference)
NIST Chemistry Reference
4H-Pyran-4-one, tetrahydro-(29943-42-8)
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Safety Information

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
10
Hazard Note 
Keep Cold/Flammable/Irritant
HazardClass 
3.2
PackingGroup 
III
HS Code 
29329995

MSDS

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Tetrahydro-4H-pyran-4-one Usage And Synthesis

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.

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.

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.

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.]

Tetrahydro-4H-pyran-4-oneSupplier

BTC Pharmaceutical CO. Ltd Gold
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