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Tetrahydro-4H-pyran-4-one Basic information
Application Description
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;4-OXOTETRAHYDROPYRAN;4-THP;TetrahydroHpyranone
CAS: 29943-42-8
MF: C5H8O2
MW: 100.12
EINECS: 249-967-2
Product Categories: Oxygen cyclic compounds;blocks;Heterocycles;Heterocycles series;Carbonyl Compounds;Pyrans, Piperidines &Piperazines;Ketone;Pyrans, Piperidines & Piperazines;Heterocycle-other series
Mol File: 29943-42-8.mol
Tetrahydro-4H-pyran-4-one Structure
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.)
Fp  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)
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
F  10
Hazard Note  Keep Cold/Flammable/Irritant
HazardClass  3.2
PackingGroup  III
HS Code  29329995
MSDS Information
Provider Language
Tetrahydro-4H-pyran-4-one English

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-one Preparation Products And Raw materials
Raw materials Ethanol-->Sodium hydroxide-->Hydrochloric acid-->Ethyl acetate-->DCM-->PETROLEUM ETHER-->Magnesium sulfate-->Acetone-->Aluminum chloride-->Diethyl oxalate-->Phosphoric acid-->Nickel-->Sodium ethoxide-->Copper-->Heptane-->Sodium phosphate monobasic-->Dibutyl phthalate-->ETHYLENE-->1,2,3,4-Tetrahydronaphthalene-->3-Chloropropionyl chloride-->2,2'-Bipyridine
Preparation Products 4-Aminotetrahydropyran hydrochloride-->2-(TETRAHYDRO-PYRAN-4-YL)-ETHANOL-->4-Aminotetrahydropyran-->E-4-Hexen-1-ol