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. 

Inert atmosphere,Room Temperature

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

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

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.

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.

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(29943-42-8)Related Product Information

• Tetrahydropyran
• Tetrahydrothiophen-3-one
• 4-Aminotetrahydropyran
• Centchroman
• Tetrahydro-4-pyranol
• 5-Formylsalicylic acid
• TETRAHYDRO-2H-PYRAN-4-YLACETYL CHLORIDE
• TETRAHYDRO-2H-PYRAN-4-CARBOXAMIDE
• Tetrahydrothiopyran-4-one
• Tetrahydro-2H-pyran-4-carboxylic acid
• Tetrahydropyranyl-4-acetic acid
• Tetrahydro-4H-Pyran-4-one
• TETRAHYDROPYRAN-2-METHANOL
• Ethyl Tetrahydropyran-4-Carboxylate
• ETHYL TETRAHYDROPYRAN-4-YL-ACETATE
• (TETRAHYDRO-FURAN-3-YL)-ACETIC ACID
• Tetrahydropyran-4-carbaldehyde
• Tetrahydro-2H-pyran-4-carbonyl chloride